Sodium borohydride → 3-Benzylbenzyl alcohol

HRID 1614455Notes

Reaction equation

HRID 1614455 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(OCC)C>CO>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 131027433-BenzylbenzaldehydeHCID 21584184Diethylether water

Product 1

HCID 5976133-Benzylbenzyl alcoholYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Benzylbenzaldehyde (5.5 g) was dissolved in methanol (75 cm3) and cooled to 0° C. Sodium borohydride (1.29 g) was added gradually in small portions, and stirring was continued for one hour. The reaction mixture was cautiously poured into a water/diethyl ether mixture, and the resulting ethereal solution was washed with water and brine, and dried over anhydrous magnesium sulphate. Evaporation of the solvents under reduced pressure gave 3-benzylbenzyl alcohol as a pale yellow oil (5.2 g). The product was used without further purification.

Workup

  1. washthe resulting ethereal solution was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-c1e47ff332e743689be6b776dd985ec0
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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