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

HRID 274063노트

반응식

HRID 274063 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
160 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f446c5a8ed9d4da7a684b5ff726c906f
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387710

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