A useful method for preparation of carboxylic acids from terminal alkynes

1983 ◽  
Vol 61 (10) ◽  
pp. 2423-2424 ◽  
Author(s):  
Suzanne R. Abrams
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Chain Length ◽  
Good Yield ◽  
Terminal Alkynes ◽  
Terminal Acetylenes ◽  
Long Chain ◽  
Acetic Acids

Substituted acetic acids can be prepared in good yield (50–80%) from terminal acetylenes of the same chain length. The alkyne is first converted to the thiophenyl ether, which is treated without purification with mercuric sulfate in acetic acid and 2 N sulfuric acid affording the carboxylic acid. The method is particularly useful in the synthesis of long chain ω-hydroxyalkanoic acids.

scholarly journals Computational notes on the electronic properties of carboxylic acid

2020 ◽  
Vol 9 (2) ◽  
pp. 1079-1082
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Electronic Properties ◽  
Carboxylic Acids ◽  
Normal Mode ◽  
Normal Modes ◽  
Carboxyl Groups ◽  
Vibrational Characteristics ◽  
Vibrational Features ◽  
Acetic Acids

The present work describing the electronic properties and vibrational characteristics of carboxylic acids. Acetic acid is chosen as model molecules then optimized at B3LYP/6-31g(d,p) level of theory. The vibrational frequencies were calculated at the same level of theory. Band assignments which were calculated as 18 normal modes were assigned as one compare the normal mode coordinates with original one. Band assignments were described indicating the directions of normal modes in terms the vibrating atoms of the acetic acids. It could be concluded that DFT could be a useful tool for elucidation both the structural and vibrational features of carboxylic acids and then further utilized for assignment of the structures contains carboxyl groups which are known as most reactive structures in chemistry, biology and environment.

Improved synthesis of anti-sesquinorbornene

1984 ◽  
Vol 62 (9) ◽  
pp. 1840-1844 ◽  
Author(s):  
Karl R. Kopecky ◽  
Alan J. Miller
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Lead Tetraacetate ◽  
Carboxyl Group ◽  
Silver Acetate ◽  
Benzenesulfonyl Chloride ◽  
Methoxide Ion ◽  
Hydrolysis Of ◽  
Monomethyl Ester

Treatment of methyl hydrogen decahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylate with lead tetraacetate in benzene – acetic acid replaces the carboxyl group by an acetoxy group. Hydrolysis of this product with 25% sulfuric acid at 130 °C forms 8a-hydroxydecahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 10. The reaction between 10 and benzenesulfonyl chloride in pyridine containing triethylamine at 95 °C produces anti-sesquinorbornene 1 in 34% yield. In the absence of triethylamine 1 is converted to the hydrochloride. The iodohydroperoxide of 1 is converted by silver acetate at 0 °C to the diketone in a luminescent reaction. The 1,2-dioxetane could not be isolated. Decahydro-1,4:5,8-exo,exo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride is converted slowly by methoxide ion in methanol at 150 °C to the monomethyl ester which then undergoes demethylation. The isomeric exo,endo anhydride undergoes reaction readily with methoxide ion at 80 °C.

A Schiff base-modified silver catalyst for efficient fixation of CO2 as carboxylic acid at ambient pressure

2017 ◽  
Vol 19 (9) ◽  
pp. 2080-2085 ◽  
Author(s):  
Zhilian Wu ◽  
Lei Sun ◽  
Qinggang Liu ◽  
Xiaofeng Yang ◽  
Xue Ye ◽  
...  
Keyword(s):  
Schiff Base ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Ambient Pressure ◽  
Terminal Alkynes ◽  
Silver Catalyst ◽  
Efficient Synthesis

A Schiff base-modified silver catalyst was developed for the direct carboxylation of terminal alkynes with CO2, enabling the efficient synthesis of valuable alkynyl carboxylic acids.

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

IX.—The Synthesis of 8-Bromo-3-methoxyfluoranthene.

1969 ◽  
Vol 68 (2) ◽  
pp. 127-137
Author(s):  
Neil Campbell ◽  
Naim M. Hasan
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acids ◽  
Good Yield ◽  
Related Compounds

SummaryA second method for the synthesis of 8-bromo-3-methoxyfluoranthene from 2-bromo-7-methoxyfluorene is described. The autoxidation of fluorene derivatives including the 9-carboxylic acids and of related compounds, particularly 4-α-cyanobenzyl-7−oxo-7H-benz[de]anthracene, is discussed. Unsuccessful attempts to prepare 3-bromofluorene-9-acetic acid in good yield are reported.

Hydrogen bonding in cyclic complexes of carboxylic acid–sulfuric acid and their atmospheric implications

RSC Advances ◽  
2016 ◽  
Vol 6 (75) ◽  
pp. 71733-71743 ◽  
Author(s):  
Hailiang Zhao ◽  
Qun Zhang ◽  
Lin Du
Keyword(s):  
Hydrogen Bonding ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Particle Formation ◽  
New Particle Formation ◽  
Ring Structures ◽  
Cyclic Complexes

Carboxylic acids form cyclic ring structures with sulfuric acid and they could potentially be important in new particle formation.

scholarly journals Synthesis of α-Hydroxyisovaleric acid (Hiv) and α-Acetyloxyisovaleric Acid (Ac-Hiv), Precursors of Aureobasidin B, with Improved Yield

2018 ◽  
Vol 6 (3) ◽  
pp. 116
Author(s):  
Rani Maharani ◽  
Andi Rahim ◽  
Herdanu Rizqullah ◽  
Nur Muhammad Miftah ◽  
Ace Tatang Hidayat ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Amino Acid ◽  
Sodium Nitrite ◽  
Good Yield ◽  
Hydroxy Acid

α-Hydroxyisovaleric acid (Ac-Hiv) and α-acetyloxyisovaleric acid (Ac-Hiv) have been successfully synthesized through a diazotisation of amino acid using sodium nitrite with the catalyst of sulfuric acid and acetic acid, respectively. In the synthesis of Hiv, Zubia et al. (2005) mentioned that 3 equivalents of sodium nitrite for the reaction gave the hydroxy acid with a good yield. However, Cohen-Arazi et al. (2008) described that 6 equivalents of sodium nitrite resulted the highest yield. In present study, a variation of equivalents of sodium nitrite (3, 4, 5, 6 eq.) were trialed for the same method of synthesis. Through several experiments, we found that 6 equivalents of sodium nitrite were the best portion among all. This finding was applied into the synthesis of protected Hiv (Ac-Hiv) that was previously reported by Maharani et al. (2017) giving 63% yield when 3 equivalent of sodium nitrite was employed. By increasing the equivalent of sodium nitrite into 6 equivalents, the Ac-Hiv can be synthesized with an improved yield (71%).

Synthesis of 6-Ethyl-1,2,9-trioxopyrrolo[3,2-f ]quinoline-8-carboxylic Acid

2013 ◽  
Vol 68 (5-6) ◽  
pp. 700-706 ◽  
Author(s):  
Randa M. Al-As’ad ◽  
Mustafa M. El-abadelah ◽  
Salim S. Sabri ◽  
Jalal A. Zahra ◽  
Wolfgang Voelter
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Good Yield ◽  
Chloral Hydrate ◽  
Hydroxylamine Hydrochloride ◽  
Carboxylic Ester ◽  
Nmr Data ◽  
Concentrated Sulfuric Acid ◽  
New Compounds

Interaction of 6-amino-1-ethyl-4-oxoquinoline-3-carboxylic ester (7) with chloral hydrate and hydroxylamine hydrochloride gave the corresponding isonitroso-acetamido derivative 8 which, upon treatment with concentrated sulfuric acid, was converted regioselectively into 1,2,9-trioxopyrrolo[ 3,2- f ]quinoline-8-carboxylic acid (3). This novel tricyclic system was isolated in good yield as a stable hydrate 3H. Structural assignments of the new compounds are based on microanalytical and spectral (MS and NMR) data

Chain Length Breakdown of Cellulose by Acetic Acid Solutions of Water and Sulfuric Acid

1958 ◽  
Vol 50 (1) ◽  
pp. 103-106
Author(s):  
C. J. Maim ◽  
K. T. Barkey ◽  
E. B. Lefferts ◽  
R. T. Gielow
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Chain Length ◽  
Acid Solutions

Molecular Cocrystals of Carboxylic Acids. IX. Carboxylic Acid Interactions With Organic Heterocyclic Bases. The Crystal Structures of the Adducts of (2,4-Dichlorophenoxy)acetic Acid With 3-Hydroxypyridine, 2,4,6-Trinitrobenzoic Acid With 2-Aminopyrimidine, and 4-Nitrobenzoic Acid With 3-Amino-1,2,4-triazole

1992 ◽  
Vol 45 (6) ◽  
pp. 969 ◽  
Author(s):  
KA Byriel ◽  
CHL Kennard ◽  
DE Lynch ◽  
G Smith ◽  
JG Thompson
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
X Ray ◽  
Nitrobenzoic Acid ◽  
Dichlorophenoxy Acetic Acid ◽  
Heterocyclic Bases

The cocrystal adducts of a number of carboxylic acids with organic heterocyclic bases have been prepared, and their structures and intermolecular interactions interpreted through X-ray diffraction and infrared spectroscopic techniques. The crystal structures of three of these compounds, the 1 : 1 adducts [{(2,4-dich1orophenoxy)acetic acid)(3-hydroxypyridine)] (1), [(2,4,6-trinitrobenzoie acid)(2-aminopyrimidine)] (2), and [(4-nitrobenzoic acid)(3-amino- 1,2,4-trimole)] (3), have been determined by single-crystal X-ray diffraction and refined to residuals R 0.026, 0.033 and 0.040 for 1814, 1531 and 727 observed reflections, respectively.

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