Methyl 4-Formylbenzoate → Methyl 4-(hydroxymethyl)benzoate

HRID 1274221Notes

Reaction equation

HRID 1274221 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 4311764Sodium borohydride

Product 1

HCID 81325Methyl 4-(hydroxymethyl)benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of p-methoxycarbonylbenzaldehyde (Description 35, 0.82 g, 5.0 mmol) in methanol (10 ml) at 0° under argon was treated with sodium borohydride (50 mg, 1.25 mmol), added in portions over 5 minutes. After stirring overnight the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and dried (MgSO4). Removal of the solvent gave the desired product as a colourless solid (0.78 g, 94%). δH (CDCl3) 1.83 (1H, t, J 5.9 Hz), 3.93 (3H, s), 4.78 (1H, d, J 5.9 Hz), 7.45 (2H, d, J 8.1 Hz), 8.04 (2H, d, J 8.1 Hz) ppm.

Workup

  1. additionadded in portions over 5 minutes
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-e89c213a29c64339bed411a464cc5f7c
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

Loading…