3-Hexen-1-ol → But-2-enoic acid hex-3-enyl ester

HRID 1621079

反応式

HRID 1621079 の反応式
[CH2:1]([OH:7])[CH2:2][CH:3]=[CH:4][CH2:5][CH3:6].[C:8](O)(=[O:12])/[CH:9]=[CH:10]/[CH3:11]>CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:1]([O:7][C:8](=[O:12])[CH:9]=[CH:10][CH3:11])[CH2:2][CH:3]=[CH:4][CH2:5][CH3:6]

参加物

5

反応物 2

HCID 109933-Hexen-1-olHCID 637090Crotonic Acid

生成物 1

HCID 103380But-2-enoic acid hex-3-enyl ester収率 82.2%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

反応条件

温度
125 °C

実験手順

Hex-3-en-1-ol (179 g), crotonic acid (181 g), PTSA (7.2 g), and toluene (250 mL) were charged into a 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a Dean-Stark trap, and a condenser. The reaction mixture was heated to reflux at about 120-130° C. Water was removed azeotropically. The reaction was aged at reflux for about 4-5 hours until no more water evolved. The reaction mixture was cooled to room temperature and quenched with water (400 mL). The organic layer was separated and subsequently washed with sodium carbonate (5%, 300 mL), and further distilled to provide but-2-enoic acid hex-3-enyl ester (247 g) with a boiling point of 109° C. at 20 mmHg.

後処理

  1. customfitted with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. customWater was removed azeotropically
  4. temperatureat reflux for about 4-5 hours until no more water
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customquenched with water (400 mL)
  7. customThe organic layer was separated
  8. washsubsequently washed with sodium carbonate (5%, 300 mL)
  9. distillationfurther distilled

出典と根拠

ORDレコード
ord-5e2798dfb17944cea50566fb0e9b83c0
出典データセット
uspto-grants-2014_07
特許番号
US08772533B1

関連ノート

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