4-Chlorobenzaldehyde → 4-(4-Chlorophenyl)butyric acid

HRID 1075194Notes

Reaction equation

HRID 1075194 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C-:10]#N.[Na+].[C:13]([O:16][CH2:17][CH3:18])(=[O:15])[CH3:14]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][CH2:10][CH2:14][C:13]([OH:16])=[O:15])=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:7])[CH2:10][CH2:14][C:13]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 8857Ethyl AcetateHCID 8929Sodium Cyanide

Product 2

HCID 2597404-(4-Chlorophenyl)butyric acidHCID 10490261Ethyl 4-(4-chlorophenyl)-4-oxobutanoate

Procedure

4-(4-Chlorophenyl)-n-butyric acid was prepared by reacting 4-chlorobenzaldehyde with ethyl acetate and sodium cyanide to provide ethyl 4-(4-chlorophenyl)-4-oxo-butyrate, hydrolyzing the ethyl butyrate derivative to afford 4-(4-chlorophenyl)-4-oxobutyric acid, and then reducing the 4-oxo-group of said acid by reaction with zinc and hydrochloric acid.

Sources & evidence

ORD record
ord-811ee4256c0d4cef8181538753689bef
Source dataset
uspto-grants-1983_07
Patent number
US04395410

Reaction notes

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