Aluminium lithium hydride → (4-Bromo-2-methylphenyl)methanol

HRID 51794Notes

Reaction equation

HRID 51794 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.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 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 LiAlH4 (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. customcarefully quenched with H2O
  2. extractionThe mixture was extracted with Et2O
  3. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dec60544f3ed41f98ec3e9bb5dcc95a4
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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