4-Bromo-2-methylbenzoic acid → (4-Bromo-2-methylphenyl)methanol

HRID 2410552Notes

Reaction equation

HRID 2410552 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 995704-Bromo-2-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanolYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-bromo-2-methylbenzoic acid (1.0 g, 4.65 mmol) in Et2O (15 mL) was added lithium aluminiumhydride (370 mg, 10.23 mmol) and the mixture was stirred for 4 hours. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (4×100 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (silica, petrol ether/EtOAc) to give the title compound as a colorless gum (752 mg, 80%). 1H NMR (CDCl3, 400 MHz) δ 7.35-7.30 (2H, m), 7.24 (1H, m), 4.65 (2H, s), 2.32 (3H, s).

Workup

  1. extractionextracted with EtOAc (4×100 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (silica, petrol ether/EtOAc)

Sources & evidence

ORD record
ord-7de532c134634ce6b74f627b45a63a97
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

Loading…