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

HRID 2185351Notes

Reaction equation

HRID 2185351 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 LiA1H4 (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 LiA1H4 (177.0 mg, 4.58 mmols)
  2. customcarefully quenched with H2O The mixture
  3. extractionwas 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-db8e484dd47843bbb816d84ebfaf0b71
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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