Methanol → 1-(2-Methylphenyl)ethanol

HRID 1362716Notes

Reaction equation

HRID 1362716 reaction equation
[BH4-].[Na+].C[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH3:13]O.O>C1COCC1.C(OCC)(=O)C>[C:12]1([CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:5]([OH:6])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 71481-Phenyl-1-propanoneHCID 4311764Sodium borohydride

Product 1

HCID 1109531-(2-Methylphenyl)ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (564 mg) was added to a solution of 2-methylacetophenone (1 g) in a mixture of THF (8 mL) with methanol (32 mL), and the reaction solution was stirred at room temperature for 20 minutes. Water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 911 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-80eb09c168644fceb5748d994639217c
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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