Methanol → (5-(Benzyloxy)-2-methylphenyl)methanol

HRID 709687Notes

Reaction equation

HRID 709687 reaction equation
[CH2:1]([O:8][C:9]1[C:10](C)=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH3:19])=[C:11]([CH2:12][OH:14])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 118068023-Benzyloxy-2-methyl-benzoic acid

Product 1

HCID 117759998(5-(Benzyloxy)-2-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(benzyloxy)-2-methylbenzoic acid (300 mg) in THF (10 mL) was added a 1.0 M solution of borane-THF complex in THF (1.85 mL) over 30 min. After stirring for 2 hr, methanol (20 mL) was added dropwise to the reaction mixture over 20 min. Methanol (10 mL) was added to the reaction mixture, and the solvent was evaporated under reduced pressure to give the title compound (280 mg) as a white solid. This compound was used for the next step without further purification.

Workup

  1. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-248f33a08b134a748204c54460a21c31
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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