4-Nitrophenol → 1-(4-Methylphenoxy)-2-(4-nitrophenoxy)-3,3,4,4,5,5-hexafluorocyclopent-1-ene

HRID 981367

反応式

HRID 981367 の反応式
F[C:2]1[C:6]([F:8])([F:7])[C:5]([F:10])([F:9])[C:4]([F:12])([F:11])[C:3]=1F.[CH3:14][C:15]1[CH:21]=[CH:20][C:18]([O-:19])=[CH:17][CH:16]=1.[Na+].[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([O-:25])=[O:24].C(N(CC)CC)C>CN(C)C=O.O>[CH3:14][C:15]1[CH:21]=[CH:20][C:18]([O:19][C:2]2[C:6]([F:8])([F:7])[C:5]([F:10])([F:9])[C:4]([F:12])([F:11])[C:3]=2[O:32][C:29]2[CH:30]=[CH:31][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 11212PerfluorocyclopenteneHCID 23673456Sodium p-methylphenolate

生成物 1

HCID 146180561-(4-Methylphenoxy)-2-(4-nitrophenoxy)-3,3,4,4,5,5-hexafluorocyclopent-1-ene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

21.2 g (0.1 mol) of perfluorocyclopentene were added dropwise at 5° C. to 13 g (0.1 mol) of sodium 4-methylphenoxide in 50 ml of dimethylformamide in the course of 15 minutes. After stirring at room temperature for 8 hours, a solution of 13.9 (0.1 mol) of 4-nitrophenol and 10.1 g of triethylamine in 50 ml of dimethylformamide was added dropwise to the reaction mixture, which was stirred for a further 6 hours at 40° C. The reaction mixture was then stirred into 300 ml of water and the organic phase was separated off after addition of 100 ml of methylene chloride. The organic phase was then washed successively with 50 ml of water, 50 ml of 5% strength hydrochloric acid and again with 50 ml of water, dried over sodium sulphate and evaporated to dryness on a rotary evaporator. The crude yield of product was 34 g. It was recrystallized from petroleum ether and 20 g of crystalline material were thus obtained, which corresponds to 47.7% of theory. The crystalline material had a melting point of 72° to 76° C. and showed a value for m/e of 419 for the molecular ion in the mass spectrum.

後処理

  1. stirringwas stirred for a further 6 hours at 40° C
  2. customthe organic phase was separated off
  3. additionafter addition of 100 ml of methylene chloride
  4. washThe organic phase was then washed successively with 50 ml of water, 50 ml of 5% strength hydrochloric acid and again with 50 ml of water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness on a rotary evaporator
  7. customIt was recrystallized from petroleum ether and 20 g of crystalline material
  8. customwere thus obtained

出典と根拠

ORDレコード
ord-65d65d4fa8eb4c9ca35b3d63d81e0050
出典データセット
uspto-grants-1991_02
特許番号
US04990633

関連ノート

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