2-Bromo-3-methylbenzoic acid → (2-Bromo-3-methylphenyl)methanol

HRID 1028980Notes

Reaction equation

HRID 1028980 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 27355882-Bromo-3-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 52987706(2-Bromo-3-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-3-methylbenzoic acid (4.0 g, 18.60 mmol) in THF (93 mL) was cooled to 0° C. and LAH (1.41 g, 37.2 mmol) added by portion. After the reaction completed, aq. K/Na tartrate was added and the reaction stirred overnight. The aqueous layer was extracted with EtOAc and the organic layer was then washed with water and brine (3× ea.), dried over Na2SO4 and concentrated in vacuo to give (2-bromo-3-methylphenyl)methanol as a clear oil that was used without further purification.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe organic layer was then washed with water and brine (3× ea.)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bb3791f8ee344d5a1de7af82da45c5f
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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