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1-Chloro-3,7-dimethyl-octa-2,6-diene → 4-Hydroxy-undecanoic Acid 3,7-dimethyl-octa-2,6-dienyl Ester

HRID 841153
ノート
印刷プレビュー

反応式

HRID 841153 の反応式
Cl[CH2:2][CH:3]=[C:4]([CH3:11])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9].[Na+].[OH:13][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:15][CH2:16][C:17]([O-:19])=[O:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:11][C:4]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:3][CH2:2][O:19][C:17](=[O:18])[CH2:16][CH2:15][CH:14]([OH:13])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 991061-Chloro-3,7-dimethyl-octa-2,6-dieneHCID 23710311Sodium 4-hydroxyundecanoate

生成物 1

HCID 542694794-Hydroxy-undecanoic Acid 3,7-dimethyl-octa-2,6-dienyl Ester収率 31.8%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 155 g 1-chloro-3,7-dimethyl-octa-2,6-diene, 202 g 4-hydroxy-undecanoic acid sodium salt and 5 g tetrabutylammoniumbromide in 800 ml of dimethylformamide was heated to 50° C. After stirring for 24 hours, the mixture was cooled to room temperature and filtered through Celite. The filtrate was diluted with ether, washed with water, 2N HCl, saturated sodium bicarbonate and brine. The organic phase was dried and evaporated to dryness. The resulting yellow oil was purified by wipe film distillation to yield 96.6 g of a yellow oil.

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. additionThe filtrate was diluted with ether
  4. washwashed with water, 2N HCl, saturated sodium bicarbonate and brine
  5. customThe organic phase was dried
  6. customevaporated to dryness
  7. customThe resulting yellow oil was purified
  8. distillationfilm distillation

出典と根拠

ORDレコード
ord-cbc6247ae96b4444acf392e2a004811d
出典データセット
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06369248B1

反応ノート

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