Condensations Brought about by Bases. IV. The Condensation of Ethyl Isobutyrate with Benzoyl Chloride, Benzoic Anhydride and Phenyl Benzoate as Examples of the Claisen Type of Condensation1

1938 ◽  
Vol 60 (8) ◽  
pp. 1960-1962 ◽  
Author(s):  
B. E. Hudson ◽  
R. H. Dick ◽  
Charles R. Hauser
1958 ◽  
Vol 11 (3) ◽  
pp. 336
Author(s):  
M Karelsky ◽  
KH Pausacker

When benzoyl peroxide was heated with phosphorus trichloride (1 and 2 mol) in benzene, or chlorobenzene solution, carbon dioxide, benzoyl chloride, and phenyl phosphonyl chloride were the major products. Diphenyl phosphonyl chloride was also formed in small yield, p-Chlorobenzoyl peroxide reacted with phosphorus trichloride, in benzene solution, yielding carbon dioxide, p-chlorobenzoyl chloride, p-chlorophenyl phosphonyl chloride, and p-chlorobenzoic anhydride. The reaction of benzoyl peroxide with phosphorus trichloride alone yielded benzoyl chloride only. Phosphorus oxychloride, on the other hand, does not enter into the reaction. Thionyl chloride, in benzene, gave a complex mixture consisting of carbon dioxide, chlorobenzene, benzoyl chloride, phenyl benzoate, benzene sulphonyl chloride, diphenyl, and benzoic anhydride. Sulphuryl chloride in benzene yielded a mixture of carbon dioxide, chlorobenzene, benzoic acid, phenyl benzoate, and diphenyl. The mechanisms of these various reactions are discussed.


To understand deeply the process of acylation of natural polyphenol gossypol, its stepwise benzoylation was performed using benzoyl chloride and benzoic anhydride as acylating agents in the presence of pyridine-N-oxides. The influence of the composition of a reaction mixture on the benzoylation process and reaction products was analyzed by the method of reversed-phase high-performance liquid chromatography. It was established that benzoylation of gossypol leads to the tautomeric transition of the respective fragment from aldehyde to lactol tautomeric form. This transition is most likely due to the breaking of the hydrogen bond C(7)–OHO=C(11) in combination with the displacement of the aldehyde group by the benzoyl fragment from the naphthyl ring plane (in the case of benzoylation of C(7)–OH group); benzoylation of C(6)–OH group is accompanied by the breaking of the hydrogen bond C(6)–OHO–C(7). These changes of configuration significantly facilitate the proton transfer from the C(1)–OH group to oxygen at C(11) followed by the formation of the lactol cycle. The use of benzoyl chloride as an acylating agent in combination with triethylamine and 4-methoxypyridine-N-oxide allows benzoylating gossypol quickly. However, the variety of formed benzoates is quite large because of the similar reactivity of different hydroxyl groups. In the case of benzoic anhydride, the number of isomeric gossypol benzoates remains quite high. Much more esters with higher retention time are accumulated due to a higher degree of benzoylation.


2000 ◽  
Vol 65 (5) ◽  
pp. 644-650 ◽  
Author(s):  
Eva Veverková ◽  
Battsengel Gotov ◽  
Róbert Mitterpach ◽  
Štefan Toma

Benzoylations of several benzene, naphthalene and thiophene derivatives with benzoyl chloride or benzoic anhydride, catalyzed with EPZG® catalyst and in the absence of solvents were studied under microwave irradiation (MWI). Reasonable to good yields of products were achieved in short times.


Author(s):  
Jenan Mohammed Ubaid ◽  
Abeer Fauzi Al-Rubaye ◽  
Imad Hadi Hameed

Methanolic extract of bioactive compounds of Trogoderma granarium was assayed. GC-MS analysis of Trogoderma granarium revealed the existence of the Pentanoic acid , 1,1-dimethylpropyl ester , (1H)-Pyrimidinone , 5-chloro-4,6- diphenyl, Cyclobutanemethanol , α-methyl- , Nitro-2-methyl-1,3-propanediol , Hydroxylamine ,O-(2-methylpropyl)- , Uridine , 2',3'-O-(phenylmethylene)- ,Acetic acid ,2-benzoylthio-,2-oxo-2-phenylethyl ester , methylpropyl)- , Uridine , 2',3'-O-(phenylmethylene)- , 5'-(4-methylbenzenesulfo , Indolinol , 1-benzoyl-, Benzeneethanol , β-methyl-,(s)- , Acetic acid ,2-benzoylthio-,2-oxo-2-phenylethyl ester , Phenacyl thiocyanate , Deoxy-L-ribose-2,5-dibenzoate , Methenamine , Alanine , N-methyl-n-propargyloxycarbonyl-, decyl ester , Benzoyl chloride , Thiophene-2-ol , benzoate , Ethanone , -(5- nitrotetrazol-2-yl)-1-phenyl- , 2,5-Dimethylhexane-2,5-dihydroperoxide , Benzamide , N-(3-benzylthio-1,2,4-thiadiazol- 5-yl)- , Methyl p-(2-phenyl-1-benzimidazolyl)benzoate , Methyl-2-phenoxyethylamine , Pentaborane(11) , cis-Methoxy- 5-trans-methyl-1R-cyclohexanol , Nitro-1-phenyl-3-(tetrahydropyran-2-yloxy)propan-1-one , cis-Methoxy-5-transmethyl-1R-cyclohexanol. Trogoderma granarium produce many important secondary metabolites with high biological activities.


2012 ◽  
Vol 68 (6) ◽  
pp. o1857-o1857 ◽  
Author(s):  
Xi-Wang Liu ◽  
Jian-Yong Li ◽  
Han Zhang ◽  
Ya-Jun Yang ◽  
Ji-Yu Zhang

The title compound, C10H5ClF2N2OS, was obtained by linking an amino heterocycle and a substituted benzoyl chloride. The dihedral angle between the two rings is 41.2 (2)° and the equalization of the amide C—N bond lengths reveals the existence of conjugation between the benzene ring and the thiazole unit. In the crystal, pairs of N—H...N hydrogen bonds link molecules into inversion dimers. Non-classical C—H...F and C—H...O hydrogen bonds stabilize the crystal structure.


1973 ◽  
Vol 22 (3-4) ◽  
pp. 271-284 ◽  
Author(s):  
J. P. Van Meter ◽  
B. H. Klanderman

1995 ◽  
Vol 34 (5) ◽  
pp. 1572-1580 ◽  
Author(s):  
Yao-Sheng Lee ◽  
Mou-Yung Yeh ◽  
Yen-Ping Shih

2017 ◽  
Vol 29 (9) ◽  
pp. 1888-1890
Author(s):  
Mohammad A. Batiha ◽  
Elena A. Chizhova ◽  
Marwan M. Batiha ◽  
Leema A. Al-Makhadmeh ◽  
Saleh Rawadieh ◽  
...  

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