Water → 4-(Phenylmethyl)benzenemethanol

HRID 1590410Notes

Reaction equation

HRID 1590410 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH2:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11345471Ethyl 4-benzylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5976144-(Phenylmethyl)benzenemethanolYield 76.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The above ester (4 g) in dry ether under nitrogen at 0° was treated with lithium aluminium hydride (0.9 g). After 1 hour at 0° and 18 hours at 25° water was added carefully and the mixture worked up in the usual manner to give 4-benzylbenzyl alcohol (2.52 g). NMR 1H: 7.21(9H,m), 4.53(2H,s), 3.95(2H,s), 2.10(1H,bs).

Sources & evidence

ORD record
ord-bf657abaa9cf4bb4802f7500eb2285fb
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

Loading…