Benzyl 4-Hydroxybenzoate → HCID 19891729, compound

HRID 727981Notes

Reaction equation

HRID 727981 reaction equation
[CH2:1]([C:12]1[CH:27]=[CH:26][C:15]([C:16]([O:18]CC2C=CC=CC=2)=[O:17])=[C:14]([C:28]([OH:30])=[O:29])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].OC1C=CC(C(OCC2C=CC=CC=2)=O)=CC=1.C(Cl)(=O)CCCCCCCCCCC>[Pd]>[CH2:1]([C:12]1[CH:27]=[CH:26][C:15]([C:16]([OH:18])=[O:17])=[C:14]([C:28]([OH:30])=[O:29])[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 8166Dodecanoyl chlorideHCID 54409710HCID 54409710, compound

Product 1

HCID 19891729HCID 19891729, compoundYield 102.5%

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.

Sources & evidence

ORD record
ord-3b495bccfef84d1896a03cadca6a6c18
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Reaction notes

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