Water → HCID 54514636、化合物

HRID 1974893ノート

反応式

HRID 1974893 の反応式
[CH3:1][C:2](O)([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:3]=[CH2:4].P(Br)(Br)[Br:18].O>CCCCCC.N1C=CC=CC=1>[Br:18][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13]

参加物

6

反応物 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 5288243,7,11-Trimethyldodec-1-en-3-ol

生成物 1

HCID 54514636HCID 54514636、化合物収率 189.9%

試薬・触媒・溶媒 2

HCID 1049Pyridine触媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

In 300 ml of hexane were dissolved 50 g of 3,7,11-trimethyl-1-dodecen-3-ol and 0.87 g of pyridine, and 30.8 g of phosphorus tribromide was added dropwise to the solution at 0° to -10° C. After 2 hours of stirring at 0° C., the reaction mixture was poured into water and extracted with hexane. The hexane layer was successively washed with aqueous sodium hydrogen carbonate and aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off to give 62.5 g of crude 1-bromo-3,7,11-trimethyl-2-dodecene. To a suspension of 14.2 g of zinc in 26 ml of acetic acid was added dropwise 62.5 g of the crude 1-bromo-3,7,11 -trimethyl-2-dodecene and the mixture was stirred at room temperature for 1 hour. Thereafter, the zinc was filtered off and the filtrate was poured into water and extracted with hexane. The hexane layer was washed with aqueous sodium hydrogen carbonate and aqueous sodium chloride in that order and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was further distilled under reduced pressure to give 10.6 g (yield 25%) of 3,7,11-trimethyl-1-dodecene. The physical constants of the compound are as follows.

後処理

  1. additionwas added dropwise to the solution at 0° to -10° C
  2. extractionextracted with hexane
  3. washThe hexane layer was successively washed with aqueous sodium hydrogen carbonate and aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

出典と根拠

ORDレコード
ord-ee8577d210554f5fb1979fd6cb4e162a
出典データセット
uspto-grants-1994_02
特許番号
US05284850

反応ノート

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