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

HRID 7468

반응식

HRID 7468 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8003Pentane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9e8621af0b5e4a71bd5b08d7280c5cb2
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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