Triphenylphosphine → Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HRID 358114

反応式

HRID 358114 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrCC(OC)=O.[Br-].[CH3:27][O:28][C:29]([CH2:31][P+:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].[PH4+].[OH-].[Na+]>C1C=CC=CC=1.O>[CH3:27][O:28][C:29]([CH:31]=[P:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:30]

参加物

8

反応物 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 60984Methyl bromoacetateHCID 2733211Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, bromide (1:1)HCID 5460504Phosphonium

生成物 1

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester収率 80%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

Triphenyl phosphine (13 g.) was dissolved in dry benzene (60 ml.) and methyl bromoacetate (8.3 g.) was added dropwise. The solution was heated at 70° C., for 2 days, and then cooled and filtered. The residue was washed with benzene and dried to give about 16 g. of (methoxycarbonyl methyl)triphenylphosphonium bromide. The phosphonium salt (B 10 g.) was dissolved in water (250 ml.) and 5% aqueous sodium hydroxide was added dropwise with stirring until the solution became alkaline to litmus. The resulting precipitate was filtered off, washed with water and dried. Crystallisation from ethyl acetate/petroleum spirit gave (methoxycarbonyl methylene) triphenyl phosphorane as a colourless solid in about 80% yield.

後処理

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe residue was washed with benzene
  4. customdried
  5. customto give about 16 g
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customCrystallisation from ethyl acetate/petroleum spirit

出典と根拠

ORDレコード
ord-b36eca86bcb04671a0d8f648a4742b63
出典データセット
uspto-grants-1984_08
特許番号
US04464391

関連ノート

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