Sodium borohydride → Racemic 1-[4-(2,3,5,6-Tetramethyl-benzyloxy)-phenyl]-propan-1-ol

HRID 1669248Notes

Reaction equation

HRID 1669248 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([CH3:24])[C:5]=1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][CH:9]=1>C1COCC1.CCO>[CH3:3][C:4]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([CH3:24])[C:5]=1[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([OH:17])[CH2:15][CH3:16])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 860854451-[4-(2,3,5,6-Tetramethyl-benzyloxy)-phenyl]-propan-1-one

Product 1

HCID 59729447Racemic 1-[4-(2,3,5,6-Tetramethyl-benzyloxy)-phenyl]-propan-1-olYield 99.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (616 mg, 16.2 mmol) is added to the solution of 1-[4-(2,3,5,6-Tetramethyl-benzyloxy)-phenyl]-propan-1-one (4.0 g, 13.5 mmol) in THF (30 mL) and EtOH (5 mL). After stirring for 2 h, the reaction is quenched by water and extracted with ethyl acetate. The solvent is removed to afford the titled compound as a white solid (4.0 g).

Workup

  1. customthe reaction is quenched by water
  2. extractionextracted with ethyl acetate
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-cf889b41231a47738879b48f92edb368
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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