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

HRID 7468

Reaction equation

HRID 7468 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

The starting material 2,4-dihydroxytoluene was prepared by adding boron tribromide (3.1 ml, 3.2 mmol) 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 solution. 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. customThe starting material 2,4-dihydroxytoluene was prepared
  2. stirringAfter stirring for 10 minutes
  3. customthe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by flash chromatography
  10. washeluting with methylene chloride/ethyl acetate (9/1)

Sources & evidence

ORD record
ord-9e8621af0b5e4a71bd5b08d7280c5cb2
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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