Water → 3-Benzyl-4-fluorobenzyl alcohol

HRID 1194036Notes

Reaction equation

HRID 1194036 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 mixure 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-da2a8514d4c1432db08341fe746378a4
Source dataset
uspto-grants-1989_03
Patent number
US04812483

Reaction notes

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