Methanol → [3-(Benzyloxy)-4-methylphenyl]methanol

HRID 709658Notes

Reaction equation

HRID 709658 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][C:17]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 229031883-(Benzyloxy)-4-methylbenzoic acid

Product 1

HCID 24721056[3-(Benzyloxy)-4-methylphenyl]methanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(benzyloxy)-4-methylbenzoic acid (2.80 g) in THF (10 mL) was added dropwise a 1.0 M solution of borane-THF complex in THF (23 mL) at room temperature over 30 min, and the mixture was stirred for 2 hr. Methanol (20 mL) was added dropwise to the reaction mixture over 20 min, and water was further added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.60 g) as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-433bb7196e21467d90e93a5e24760372
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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