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

HRID 1936143Notes

Reaction equation

HRID 1936143 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-0c337faf5b824794843be1557c109e22
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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