Triphenylphosphine → (6-Carboxyhexyl)triphenylphosphonium bromide

HRID 1283188

반응식

HRID 1283188 반응식
[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]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 1217237-Bromoheptanoic acid

생성물 1

HCID 11027094(6-Carboxyhexyl)triphenylphosphonium bromide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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°

출처 및 근거

ORD 기록
ord-b8900420f844424cab3546fe01a7b423
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03974195

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