Triphenylphosphine → (6-Carboxyhexyl)triphenylphosphonium bromide

HRID 1283188ノート

反応式

HRID 1283188 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 11027094(6-Carboxyhexyl)triphenylphosphonium 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 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 forming a crystal, the mixture is allowed to stand overnight. The solid which separates is collected by filtration giving 134.1 g. of the product as white prisms, melting point 185°-187° C. 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. customAfter forming a crystal
  5. filtrationThe solid which separates is collected by filtration
  6. customgiving 134.1 g
  7. 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-b8900420f844424cab3546fe01a7b423
出典データセット
uspto-grants-1976_08
特許番号
US03974195

反応ノート

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