The preparation and photolysis of (E)-1-Aryl-3-methyl-3-phenylbut-1-enes

1983 ◽  
Vol 36 (3) ◽  
pp. 565 ◽  
Author(s):  
JW Blunt ◽  
JM Coxon ◽  
WT Robinson ◽  
HA Schuyt
Keyword(s):  
Reaction Time ◽  
Benzyl Alcohol ◽  
Sulfonic Acid ◽  
Reaction Times ◽  
Grignard Reaction ◽  
Aryl Substituent ◽  
Reaction Conditions ◽  
Careful Choice ◽  
Short Reaction Time ◽  
Toluene Sulfonic Acid

Reaction of 2-methyl-2-phenylpropylmagnesium chloride with benzaldehyde in tetrahydrofuran gave 2,7-dimethyl-2,4,5,7-tetraphenyloctane-4,5-diol as a 1 : 2 mixture of clear transparent crystalline plates (meso) and needles (�), 3-methyl-1,3-diphenylbutan-1-one, benzyl alcohol, 2-methyl-2-phenylpropaneand a low yield of 3-methyl-1,3-diphenylbutan-1-ol. The distinction between the meso and the (+)- diols was unequivocal because the unique space group of the former requires thedimeric molecules to lie about a crystallographic centre of symmetry. The mechanism involved in the formation of the products of the Grignard reaction is examined. By careful choice of reaction conditions a series of I-aryl-3-methyl-3-phenylbutan-1-ols were prepared. Dehydration of the 1-aryl-3-methyl-3-phenylbutan-1-ols with p-toluene sulfonic acid and a short reaction time gives(E)-1-aryl-3-methyl-3-phenylbut-1-enes but longer reaction times afford 3-aryl-1,1-dimethylindanes.Photolysis of the (E)-1-aryl-3-methyl-3-phenylbut-1-enes affords (Z)-1-aryl-3-methyl-3-phenylbut-1-enes and trans-1-aryl-3,3-dimethyl-2-phenylcyclopropanes. Extended photolysis gives 4-aryl-2-methyl-3-phenylbut-1-enes via trans-1-aryl-3,3-dimethyl-2-phenylcyclopropane by rupture of the cyclopropyl bond adjacent to the aryl substituent.

scholarly journals A Simple and Green Protocol for 2H-Indazolo[2,1-b]phthalazine-triones Using Grinding Method

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Xiao-chuan Jia ◽  
Jing Li ◽  
Yu Ding ◽  
Bin Zhang ◽  
Na Wang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Sulfonic Acid ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Short Reaction Time ◽  
Green Protocol ◽  
Simple Operation ◽  
Grinding Method ◽  
Toluene Sulfonic Acid ◽  
High Yields

A robust, facile, and solvent-free route for the three-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones in the presence of a catalytic amount ofp-toluene sulfonic acid utilizing grinding has been developed. Short reaction time, simple operation, and high yields are the advantages of this protocol.

Study on Synthesis of Ester of Citric Acid and Palmityl Alcohol

2014 ◽  
Vol 900 ◽  
pp. 361-364
Author(s):  
Xiao Hui Wang ◽  
Xi Hua Du ◽  
Li Min Dong
Keyword(s):  
Reaction Time ◽  
Citric Acid ◽  
Cation Exchange ◽  
Sulfonic Acid ◽  
Exchange Resin ◽  
Cation Exchange Resin ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Process Conditions ◽  
Toluene Sulfonic Acid

Esters of Citric acid and palmityl alcohol were synthesized by esterification reaction under catalysis of cation exchange resin and P-toluene sulfonic acid respectively. The effects of amount of catalyst, ratio of raw materials, reaction time and temperature on the synthesis reaction were investigated . The experimental results showed that optimum of process conditions were 1:1~1:1.5 molar ratio of citric acid and palmityl alcohol, reaction temperature of 130~140°C, reaction time of 2 h. Conversion of palmityl alcohol were all more than 90% under 0.3% dosage using p-toluene sulfonic acid as the catalyst, or 0.5% dosage using 721 cation exchange resin with sulfonic acid type as catalyst. The synthesized product had good surface activity.

Efficient Copper-Catalyzed Synthesis of Substituted Pyrazoles at Room Temperature

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2689-2692 ◽  
Author(s):  
Haifeng Wang ◽  
Xiangli Sun ◽  
Shuangling Zhang ◽  
Guanglu Liu ◽  
Chunjie Wang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Catalytic System ◽  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
Condensation Reaction ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Acid Catalyzed ◽  
Substituted Pyrazoles

An efficient method for the synthesis of pyrazoles through a copper-catalyzed condensation reaction has been developed. The new catalytic system not only maintained a broad substrate scope but was also active under acid-free reaction conditions, overcoming the conventional requirement for an acid-catalyzed system. Furthermore, the copper catalyst enabled this reaction to be performed at room temperature and in a short reaction time.

The Hofmann reaction involving annulation of o-(pyridin-2-yl)aryl amides selectively and rapidly leads to potential photocatalytically active 6H-pyrido[1,2-c]quinazolin-6-one derivatives

2020 ◽  
Vol 22 (22) ◽  
pp. 7955-7961
Author(s):  
Wenjing Gao ◽  
Yameng Wan ◽  
Zhiguo Zhang ◽  
Hao Wu ◽  
Tongxin Liu ◽  
...  
Keyword(s):  
Reaction Time ◽  
Reaction Conditions ◽  
Short Reaction Time

An intramolecular Hofmann reaction leads to diverse photocatalytically active 6H-pyrido[1,2-c] quinazolin-6-one derivatives with the advantages of mild reaction conditions, short reaction time, excellent yields, broad substrate scope and high FG tolerance.

scholarly journals Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

2019 ◽  
Vol 31 (4) ◽  
pp. 829-833
Author(s):  
D.S. Bhagat ◽  
S.G. Pande ◽  
M.V. Katariya ◽  
R.P. Pawar ◽  
P.S. Kendrekar
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Aryl Aldehydes ◽  
Microwave Assisted ◽  
Novel Catalyst ◽  
Work Up

One-pot efficient protocol to the synthesis of 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives via condensation of various aryl aldehydes, dicyanomethane and 4-hydroxycoumarin in presence of Emim hydroxide as an excellent homogeneous liquid catalyst. The key advantages of this methodology are mild reaction conditions, novel catalyst, short reaction time, eco-friendly, easy work-up procedure and high yield of isolation of derivatives.

Rapid synthesis of homoallylic alcohol from aldehyde with allyltributylstannane under solvent-free conditions

2012 ◽  
Vol 90 (2) ◽  
pp. 167-172 ◽  
Author(s):  
Pranjal P. Bora ◽  
H. Atoholi Sema ◽  
Barisha Wahlang ◽  
Ghanashyam Bez
Keyword(s):  
Reaction Time ◽  
Phosphotungstic Acid ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Reaction Conditions ◽  
Rapid Synthesis ◽  
Short Reaction Time ◽  
Solvent Free Conditions ◽  
Solvent Free Reaction

A catalytic amount (2 mol %) of phosphotungstic acid (PTA) is sufficient to synthesize homoallylic alcohol in excellent yields from aldehyde with allyltributylstannane upon grinding under solvent-free reaction conditions. Easy handling, very short reaction time, solvent-free reaction conditions, and aqueous workup free isolation protocol may make our method very useful for synthetic chemists.

scholarly journals Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Maryam Kamalzare ◽  
Mohammad Reza Ahghari ◽  
Mohammad Bayat ◽  
Ali Maleki
Keyword(s):  
Reaction Time ◽  
Tannic Acid ◽  
High Performance ◽  
Catalytic Performance ◽  
Natural Material ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
High Yields

AbstractRecently magnetic nanocatalyst has attracted considerable attention because of its unique properties, including high performance, easy separation from the reaction mixture, and recyclability. In this study, a novel magnetic bionanocomposite was synthesized with chitosan and tannic acid as a natural material. The synthesized bionanocatalyst was characterized by essential analysis. Fe3O4@chitosan-tannic acid as a heterogeneous nanocatalyst was successfully applied to synthesize pyranopyrazole and its derivatives by a one-pot four-component reaction of malononitrile, ethyl acetoacetate, hydrazine hydrate, and various aromatic aldehyde. At the end of the reaction, the nanocatalyst was separated from the reaction mixture and was reused several times with no significant decrease in its catalytic performance. Simple purification of products, the ability for recovering and reusing the nanocatalyst, eco-friendliness, high yields of pure products, mild reaction conditions, short reaction time, non-toxicity, economically affordable are some of the advantages of using the fabricated nanocatalyst in the synthesis of pyranopyrazole.

scholarly journals Fast and Green Method to Synthesis of Quinolone Carboxylic Acid Derivatives Using Giant-Ball Nanoporous Isopolyoxomolybdate as Highly Efficient Recyclable Catalyst in Refluxing Water

2017 ◽  
Vol 61 (1) ◽  
Author(s):  
Yahya Mirzaie ◽  
Jalil Lari ◽  
Hooshang Vahedi ◽  
Mohammad Hakimi ◽  
Ahmad Nakhaei ◽  
...  
Keyword(s):  
Reaction Time ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Reaction Times ◽  
Green Method ◽  
Direct Amination ◽  
Short Reaction Time ◽  
Piperazine Derivatives ◽  
Type Giant ◽  
Catalytic Cycles

Various potentials antibacterial fluoroquinolone compounds were prepared by the direct amination of 7-halo-6- fluoroquinolone-3-carboxylic acids with variety of piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b] pyridine using (NH<sub>4</sub>)<sub>42</sub> [Mo<sup>VI</sup><sub>72</sub>Mo<sup>V</sup><sub>60</sub>O<sub>372</sub>(CH<sub>3</sub>COO)<sub>30</sub>(H<sub>2</sub>O)<sub>72</sub>], a Keplerate-type giant-ball nanoporous isopolyoxomolybdate, as a catalyst in refluxing water. The results showed that this catalyst acts as effective catalyst and the reaction proceeded more easily and gave the highest yields of the products in short reaction time under refluxing water. Short reaction times, simple isolation of the products, and usage of eco-friendly catalysts are some features of this procedure. In addition, the catalysts was easily recovered and used in multiple catalytic cycles. This material was prepared according to a previously published literature procedure using inexpensive and readily available starting materials.

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110458
Author(s):  
Le Nhat Thuy Giang ◽  
Dang Thi Tuyet Anh ◽  
Hoang Thi Phuong ◽  
Nguyen Ha Thanh ◽  
Nguyen Thi Quynh Giang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Basic Catalyst ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Short Reaction Time ◽  
Convenient Approach ◽  
First Time

For the first time the 4-dimethylaminopyridine (DMAP) catalyzed straightforward and efficient procedure has been developed for the synthesis of 3,3′-(arylmethylene) bis(2-hydroxynaphthalene-1,4-dione) derivatives starting from lawsone (2-hydroxy-1,4-naphthoquinone) and a variety of (hetero)aromatic aldehydes in ethanol under microwave irradiation. Three of nine synthesized compounds are new. This method provides notable advantages over existing procedures including use of non-traditional basic catalyst and environmentally benign solvent, mild reaction conditions, excellent yields, short reaction time and simple workup.

A clean, simple and efficient synthesis of trans-[3-(aryl)-2,3-dihydrofuro[3,2-h] quinolin-2-yl]-(4-chlorophenyl)methanones

2017 ◽  
Vol 41 (7) ◽  
pp. 380-383
Author(s):  
Maryam Salari ◽  
Alireza Hassanabadi ◽  
Mohammad H. Mosslemin
Keyword(s):  
Reaction Time ◽  
Green Chemistry ◽  
Aromatic Aldehyde ◽  
Efficient Method ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
High Yields

We report a green and efficient method for the synthesis of trans-[3-(aryl)-2,3-dihydrofuro[3,2- h]quinolin-2-yl]-(4-chlorophenyl) methanones from the condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 8-hydroxyquinoline and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water at reflux conditions. This new protocol employing choline hydroxide, which is a green and inexpensive catalyst, offers advantages such as mild reaction conditions, short reaction time, high yields and does not involve any hazardous solvent. Therefore, this procedure can be classified as green chemistry.

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