HCID 19824462, compound → HCID 19824463, compound

HRID 727983Notes

Reaction equation

HRID 727983 reaction equation
[CH2:1]([C:12]1[CH:36]=[CH:35][C:15]([C:16]([O:18][C:19]2[CH:34]=[CH:33][C:22]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])=[CH:21][CH:20]=2)=[O:17])=[C:14]([C:37]([OH:39])=[O:38])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>[Pd]>[CH2:1]([C:12]1[CH:36]=[CH:35][C:15]([C:16]([O:18][C:19]2[CH:34]=[CH:33][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)=[O:17])=[C:14]([C:37]([OH:39])=[O:38])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 1

HCID 19824462HCID 19824462, compound

Product 1

HCID 19824463HCID 19824463, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By customary procedures, 3.5 g of benzyl 4-undecylcarboxybenzoate was prepared from 2.3 g of benzyl 4-hydroxybenzoate and 2.5 g of lauric acid chloride, and this ester was catalytically reduced under a hydrogen pressure of 2 kg/cm2 by using Pd/C as the catalyst to obtain 2.8 g of 4-undecylcarboxybenzoic acid. The acid was converted to 4-undecylcarboxybenzoic acid chloride by thionyl chloride and the acid chloride was reacted with 1.8 g of benzyl 4-hydroxybenzoate to form benzyl 4-(4-undecylcarboxybenzoyloxy)benzoate. The ester was catalytically reduced under a hydrogen pressure of 2 kg/cm2 by using Pd/C as the catalyst to isolate the benzyl group and obtain 3.0 g of 4-(4'undecylcarboxybenzoyloxy)benzoic acid.

Workup

  1. customto isolate the benzyl group

Sources & evidence

ORD record
ord-4324c6caccff4871989da802cf527d71
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Reaction notes

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