Water → 3-Benzyl-4-fluorobenzyl alcohol

HRID 483741Notes

Reaction equation

HRID 483741 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[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][C:15]=1[F:16])[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 138542803-Benzyl-4-fluorobenzaldehyde

Product 1

HCID 138542813-Benzyl-4-fluorobenzyl alcoholYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-benzyl-4-fluorobenzaldehyde (5 g) in methanol (75 cm3) was cooled to 0° C. Sodium borohydride (1.34 g) was added in portions, and the mixture stirred for 1 hour. The reaction mixture was then poured cautiously into a mixture of water and diethyl ether, and the organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulphate. Evaporation of the solvents under reduced pressure gave a pale yellow oil which was purified by distillation in a kugelrohr apparatus to give 3-benzyl-4-fluorobenzyl alcohol (4.0 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customEvaporation of the solvents under reduced pressure
  5. customgave a pale yellow oil which
  6. distillationwas purified by distillation in a kugelrohr apparatus

Sources & evidence

ORD record
ord-0ce8d2904ac845a6af28424fb246a16f
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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