Sodium borohydride → N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

HRID 1762183Notes

Reaction equation

HRID 1762183 reaction equation
[BH4-].[Na+].[C:3]([NH:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[C:9]([CH3:15])[CH:8]=1)(=[O:5])[CH3:4]>CO>[C:3]([NH:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[C:9]([CH3:15])[CH:8]=1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12931765N-(4-Formyl-3-methylphenyl)acetamide

Product 1

HCID 54053024N-[4-(hydroxymethyl)-3-methylphenyl]acetamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.248 g) was added portionwise to a solution of 4-acetamido-2-methyl benzaldehyde (2.58 g) in methanol (26 ml) with ice-cooling. After being stirred for 3 hours, the mixture was evaporated in vacuo and the residue was washed with water and dried to give 4-acetamido-2-methylbenzyl alcohol (2.22 g).

Workup

  1. temperaturecooling
  2. customthe mixture was evaporated in vacuo
  3. washthe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-d194634adfe44627bfb441d2d55db725
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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