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

HRID 634646

反応式

HRID 634646 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

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d2fd74345c4a49e39ad7d08c2cf56c2b
出典データセット
uspto-grants-2001_02
特許番号
US06184225B2

関連ノート

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