2-(ALLYLOXY)-5-BROMOBENZALDEHYDE → 5-Bromo-2-(2-propen-1-yloxy)benzenemethanol

HRID 427745Notes

Reaction equation

HRID 427745 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:6]=1[CH:7]=[O:8])[CH:2]=[CH2:3].[BH4-].[Na+]>O>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:6]=1[CH2:7][OH:8])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 21687062-(ALLYLOXY)-5-BROMOBENZALDEHYDEHCID 4311764Sodium borohydride

Product 1

HCID 21940165-Bromo-2-(2-propen-1-yloxy)benzenemethanolYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-allyloxy-5-bromobenzaldehyde (5.27 g, 21.9 mM) was treated with sodium borohydride, (0.415 g, 10.9 mM). The reaction was stirred at ambient temperature for 2½ hours, water was added and the solvent removed at reduced pressure. The residue was acidified to pH 1 and extracted with ethyl acetate twice. The organic layers were combined, dried (MgSO4) and evaporated to give 2-allyloxy-5-bromobenzyl alcohol (5.12 g, 96%) as a white solid.

Workup

  1. customthe solvent removed at reduced pressure
  2. extractionextracted with ethyl acetate twice
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-bcc2311219824dc0a77306fed58043f6
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

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