Sodium borohydride → Benzenemethanol, 5-bromo-2-(methoxymethoxy)-

HRID 862056Notes

Reaction equation

HRID 862056 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7][OH:8]

Participants

4

Procedure

To a solution of 5-bromo-2-methoxymethoxybenzaldehyde (5.00 g) in methanol (50 ml) was added, at 0° C., sodium borohydride (0.46 g). The mixture was stirred for 30 minutes at the same temperature, which was then concentrated. To the concentrate was added ethyl acetate, and the mixture was washed with an aqueous solution of potassium hydrogensulfate and a saturated aqueous saline solution, successively. The organic layer was dried (anhydrous magnesium sulfate), which was then concentrated to leave 5-bromo-2-methoxymethoxybenzyl alcohol (5.04 g) as a pale yellow oily product.

Workup

  1. concentrationwas then concentrated
  2. additionTo the concentrate was added ethyl acetate
  3. washthe mixture was washed with an aqueous solution of potassium hydrogensulfate
  4. dry with materialThe organic layer was dried (anhydrous magnesium sulfate), which
  5. concentrationwas then concentrated

Sources & evidence

ORD record
ord-0a810795ea7145fd8dc67a46d3fa7d98
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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