Ethyl Acetate → 1,3-Benzenediol, 4-methyl-

HRID 634646

Reaction equation

HRID 634646 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[C:11]([O:13]C)[CH:10]=[CH:9][C:8]=1[CH3:15].C(OCC)(=O)C.[OH-].[Na+]>CCCCC>[OH:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[CH3:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 96403Benzene, 2,4-dimethoxy-1-methyl-

Product 1

HCID 103331,3-Benzenediol, 4-methyl-Yield 94.1%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Boron tribromide (3.1 ml, 3.2 mmol) was added to a solution of 2,4-dimethoxytoluene (1 g, 6.5 mmol) in pentane (10 ml) at −70° C. The reaction mixture was allowed to warm to ambient temperature and the mixture stirred for a further 2 hours. Ice water and ethyl acetate were then added and the aqueous layer basified to pH9.5 with 2M aqueous sodium hydroxide. After stirring for 10 minutes, the organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic extract was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by flash chromatography eluting with methylene chloride/ethyl acetate (9/1) to give 2,4-dihydroxytoluene (759 mg, 94%) as a white solid.

Workup

  1. stirringAfter stirring for 10 minutes
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with methylene chloride/ethyl acetate (9/1)

Sources & evidence

ORD record
ord-d2fd74345c4a49e39ad7d08c2cf56c2b
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Linked notes

Loading…