1,4-Cyclohexanediol → HCID 15096979、化合物

HRID 345560

反応式

HRID 345560 の反応式
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]>CN(C)C=O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([O:7][CH:4]2[CH2:5][CH2:6][CH:1]([OH:8])[CH2:2][CH2:3]2)=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1

参加物

5

反応物 3

HCID 111621,4-CyclohexanediolHCID 24758Sodium hydrideHCID 677672,5-Difluoronitrobenzene

生成物 1

HCID 15096979HCID 15096979、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of 46.46 parts of 1,4-cyclohexanediol and 135 parts of N,N-dimethylformamide were added 5.28 parts of sodium hydride dispersion 50% at a temperature below 20° C. Stirring was continued for 2 hours at room temperature under nitrogen atmosphere. Then there were added dropwise 15.9 parts of 1,4-difluoro-2-nitrobenzene at about 20° C. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured onto water. The precipitated product was filtered off and taken up in trichloromethane. The solution was washed with water, dried, filtered and evaporated. The residue was boiled in 2-propanol. Upon cooling, the precipitate was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in petroleumether. The product was filtered off and dried, yielding 17.1 parts of 4-(4-fluoro-2-nitrophenoxy)cyclohexanol; mp. 150.8° C. (intermediate 85).

後処理

  1. stirringUpon completion, stirring
  2. waitwas continued overnight at room temperature
  3. additionThe reaction mixture was poured onto water
  4. filtrationThe precipitated product was filtered off
  5. washThe solution was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. temperatureUpon cooling
  10. filtrationthe precipitate was filtered off
  11. customthe filtrate was evaporated
  12. customThe residue was purified by column-chromatography over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe pure fractions were collected
  15. customthe eluent was evaporated
  16. stirringThe residue was stirred in petroleumether
  17. filtrationThe product was filtered off
  18. customdried

出典と根拠

ORDレコード
ord-cda535e558c14d91881ce6da9ba147d0
出典データセット
uspto-grants-1991_10
特許番号
US05057525

関連ノート

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