Methanol → (3-Benzyloxy-2-methyl-phenyl)-methanol

HRID 709705Notes

Reaction equation

HRID 709705 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:18])=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 118068023-Benzyloxy-2-methyl-benzoic acid

Product 1

HCID 58087471(3-Benzyloxy-2-methyl-phenyl)-methanolYield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(benzyloxy)-2-methylbenzoic acid (800 mg) in THF (10 mL) was added dropwise a 1.0 M solution of borane-THF complex in THF (6.6 mL) at room temperature over 30 min, and the mixture was stirred at room temperature for 2 hr. Methanol (10 mL) was added to the reaction mixture under ice-cooling, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (480 mg) as a white solid.

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b101e459d3974cbc83b125e3ecbe5ede
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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