Benzyl 4-Hydroxybenzoate → HCID 19824462, compound

HRID 727982Notes

Reaction equation

[CH2:1]([C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[C:14]([C:21]([OH:23])=[O:22])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].S(Cl)(Cl)=O.[OH:28][C:29]1[CH:44]=[CH:43][C:32]([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])=[CH:31][CH:30]=1>>[CH2:1]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([O:28][C:29]2[CH:44]=[CH:43][C:32]([C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])=[CH:31][CH:30]=2)=[O:17])=[C:14]([C:21]([OH:23])=[O:22])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

Reactant 3

HCID 7180Benzyl 4-Hydroxybenzoate

HCID 24386Thionyl Chloride

HCID 54415999HCID 54415999, compound

Product 1

HCID 19824462HCID 19824462, compound

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.

Sources & evidence

ORD record: ord-0347ab23da264d268831fa4d0dee2a02
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05045228

Reaction notes

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