Water → 2-nitro-6,7-dihydro-5H-benzocycloheptene

HRID 274063ノート

反応式

HRID 274063 の反応式
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:12](O)[C:6]=2[CH:5]=1)([O-:3])=[O:2].S([O-])(O)(=O)=O.[K+].O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 962WaterHCID 516920Potassium bisulfateHCID 223918023-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol

生成物 1

HCID 200948392-nitro-6,7-dihydro-5H-benzocycloheptene収率 74.5%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

A mixture of 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (70.67 g) and potassium hydrogensulfate (53.00 g) was heated at 160° C. for 1 hour. After cooling, to the mixture was added a mixture of water (400 ml) and ethyl acetate (400 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layer was washed with brine (150 ml), dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and chloroform (1:1) as an eluent to give 2-nitro-6,7-dihydro-5H-benzocycloheptene (48.1 g).

後処理

  1. temperatureAfter cooling, to the mixture
  2. additionwas added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (200 ml)
  5. washThe combined organic layer was washed with brine (150 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and chloroform (1:1) as an eluent

出典と根拠

ORDレコード
ord-f446c5a8ed9d4da7a684b5ff726c906f
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

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