Acetyl--valeric Acid

Ethyl glycidyl ether Phenyl glycidyl ether 

Submitted by J. R. Schaeffer and A. O. Snoddy.1 Checked by Richard T. Arnold and H. W. Turner. 

A solution of 368 g. of 96% sulfuric acid in 664 ml. of water is cooled to room temperature and placed in a 3-1. three-necked 

Eastman Kodak Company practical grade 2-methylcyclo-hexanol was used in this preparation. 

Technical grade chromic oxide (99.5% Cr03) in flake form was used. 

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Acetylene, purification, 39, 58 Acetylene, diphenyl-, 34, 42 y-hydroxypropyl, 33, 68 Acetylenedicarboxyuc acid, dimethyl ESTER, 32, SS Acetylenic glycols, 39, 57 2- -Acetylphenylhydroquinone, 34,1 S-Acetyl- -valeric acid, 31, 3 Acid chlorides, 39, 19 synthesis of, 37, 69... 

The fore-run and the still residue contain some 5-acetyl- -valeric acid. These fractions may be combined and redistilled to yield an additional 5-10% of 5-acetyl-w-valeric acid, but the low cost of the starting materials and the ease of preparing the crude 5-acetyl-w-valeric acid scarcely justify the labor unless a considerable number of batches are being prepared. 

Acetic acid has been found to react with toluene to form p-methylace-tophenone (Simons et al., 49), to react with benzene to form acetophenone, and to react with phenol to form p-hydroxy acetophenone. Acetyl chloride also formed acetophenone with benzene and acetic anhydride reacted with toluene to form both p-methylacetophenone and 2,4-diace-tyltoluene. Valeric acid reacted with toluene to form p-tolyl-n-butyl ketone. Both benzoic acid and benzoyl chloride reacted with toluene to form p-tolylphenyl ketone. Acenaphthene with either benzoic acid or benzoyl chloride gave 3-benzoylacenaphthene (Fieser and Hershberg,... 

A liquid-liquid continuous extractor is convenient for extracting the crude acid from the aqueous solution. With such apparatus, it is possible to extract all the crude 5-acetyl-w-valeric acid from the aqueous acid in 6-8 hours. 

Acetyl-n-valeric acid has been prepared by the oxidation of 1-methylcyclohexene with potassium permanganate 5 by the oxidation of 2-methylcyclohexanone with chromic oxide and sulfuric acid 6 by the reaction of methylzinc iodide on the ethyl ester of adipic acid chloride and saponification of the ethyl ester of 5-acetyl-w-valeric acid so obtained 7 by the saponification of the ethyl ester of diacetylvaleric acid 2 and through the hydrolysis of ethyl a-acetyl-6-cyanovalerate with boiling 20% hydrochloric acid.3... 

Acetylphenylhydroquinone, 34, 1 5-Acetyl-k-valeric acid, 31, 3 Acid chlorides, synthesis of, 37, 69 Acid isomerization of diterpenic acids,... 

The first synthesis of rfZ-deoxynupharidine was reported by Kotake et al. (30). The starting material w as 2,5-lutidine which was made to react with formaldehyde to give the diol XXVII on dehydration, acetylation, and condensation with malonic ester XXVII afforded the diester XXVIII. On hydrogenation and acid hydrolysis XXVIII was decarboxylated to the valeric acid derivative XXIX. After esterification the acid was acylated with 3-furoyl chloride and distilled with soda lime to yield dehydrodeoxynupharidine (XXX), and this on hydrogenation gave dl-deoxynupharidine (II). 

Valeric acid, a-ACETYL- -CHLORO-7-HYDROXY-, y-LACTONE, 31, 1 5-HYDROXY-3-METHYL, 5-LACTONE,... 

Valeric acid, a-ACETYL-5-CHLORO-y-HYDROXY-, 7-LACTONE, 31, 1 S-HYDROXY-3-METHYL-5-LACTONE, 35, 86... 

Valeric acid, ol-acetyl-S-chloro-y-hydroxy-, y-lactone, 31,1 Vanillic acid, 30,101,103 Vanillin, 30, 102, 104 Veratraldehyde, 31, 58 Vinyl acetate, 30, 106 Vinyl caprate, 30,108 Vinyl caproate, 30,108 Vinyl caprylate, 30,108 Vinyl 10-hendecenoate, 30,108 Vinyl laurate, 30,106 Vinyl myristate, 30,108 Vinyl oleate, 30, 108 Vinyl palmitate, 30,108 Vinyl pelargonate, 30, 108 Vinyl stearate, 30,108 Vinyl undecylenate, 30,108... 

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