2-(Benzyloxy)-5-bromobenzaldehyde → (2-(Benzyloxy)-5-bromophenyl)methanol

HRID 1870756Notes

Reaction equation

HRID 1870756 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 897136(2-(Benzyloxy)-5-bromophenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-benzyloxy-5-bromobenzaldehyde (14.5 g, 50.2 mmol) in absolute ethanol (250 ml) was treated with sodium borohydride (2.6 g, 68.8 mmol). The reaction was stirred and the temperature slowly rose to 33° C. After 1 hour the reaction mixture was evaporated and the residue dissolved in ethyl acetate and poured into a mixture of ice water (200 ml) and 1N HCl (25 ml). The organic layer was separated, washed with aqueous sodium hydrogen carbonate, brine, dried (Na2SO4) and evaporated to give 2-benzyloxy-5-bromobenzylalcohol as a pale yellow oil (14.85 g, quantitative).

Workup

  1. customslowly rose to 33° C
  2. customAfter 1 hour the reaction mixture was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. additionpoured into a mixture of ice water (200 ml) and 1N HCl (25 ml)
  5. customThe organic layer was separated
  6. washwashed with aqueous sodium hydrogen carbonate, brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-f963793d536a45998f388e06529ae378
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

Loading…