Methyl 4-bromo-2-methylbenzoate → (4-Bromo-2-methylphenyl)methanol

HRID 1069984Notes

Reaction equation

HRID 1069984 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([CH3:12])[CH:3]=1>CCOCC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([CH3:12])[CH:3]=1

Participants

3

Reactant 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl 4-bromo-2-methyl-benzoate (1.05 g, 4.58 mmols) in 10 mL of Et2O was cooled to 0° C. and treated with LiAIH4 (177.0 mg, 4.58 mmols), stirred for 3 hours, and then carefully quenched with H2O. The mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. The title compound, 830.0 mg (90%), was isolated by column chromatography (10-30% EtOAc-hexanes) as a colorless oil.

Workup

  1. additiontreated with LiAIH4 (177.0 mg, 4.58 mmols)
  2. customcarefully quenched with H2O
  3. extractionThe mixture was extracted with Et2O
  4. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b393034aa3d74439a38e9e10513e33fe
Source dataset
uspto-grants-2001_06
Patent number
US06252090B1

Reaction notes

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