Triphenylphosphine → Phosphonium, (6-carboxyhexyl)triphenyl-, bromide

HRID 262807

反応式

HRID 262807 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[Br-:1].[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([OH:10])=[O:9]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 1217237-Bromoheptanoic acid

生成物 1

HCID 11027094Phosphonium, (6-carboxyhexyl)triphenyl-, bromide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 63.6 g. of 7-bromoheptanoic acid in 80 g. of triphenylphosphine, and 300 ml. of acetonitrile is refluxed for 68 hours. Then 200 ml. of acetonitrile is removed by distillation. After the remaining solution has cooled to room temperature, 300 ml. of benzene is added with stirring. After adding a seed crystal, the mixture is allowed to stand overnight. The solid which separated is collected by filtration giving 134.1 g. of the product as white prisms, melting point 185°-187°. A portion is recrystallized from methanol-ether affording white prisms, melting point 185°-187°. The infrared spectrum shows absorptions at 2850, 2570, 2480, 1710, 1585, 1485, 1235, 1200, 1185, 1160, 1115, 1000, 755, 725, and 695 cm.-1NMR peaks are observed at 1.2-1.9, 2.1-2.6, 3.3-4.0, and 7.7-8.0 δ.

後処理

  1. additionA mixture of 63.6 g
  2. customof acetonitrile is removed by distillation
  3. additionof benzene is added
  4. additionAfter adding a seed crystal
  5. customThe solid which separated
  6. filtrationis collected by filtration
  7. customgiving 134.1 g
  8. customA portion is recrystallized from methanol-ether affording white prisms, melting point 185°-187°

出典と根拠

ORDレコード
ord-29d0759d2f364f3a861ab51221b2f31d
出典データセット
uspto-grants-1979_05
特許番号
US04154950

関連ノート

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