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

HRID 7468

反応式

HRID 7468 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8003Pentane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9e8621af0b5e4a71bd5b08d7280c5cb2
出典データセット
uspto-grants-2006_08
特許番号
US07087602B2

関連ノート

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