p-Toluenesulfonic acid → But-2-enoic acid 1,5-dimethyl-hex-4-enyl ester

HRID 1627975

반응식

HRID 1627975 반응식
[CH3:1][C:2]([CH3:9])=[CH:3][CH2:4][CH2:5][CH:6]([OH:8])[CH3:7].[C:10](O)(=[O:14])/[CH:11]=[CH:12]/[CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:7][CH:6]([O:8][C:10](=[O:14])[CH:11]=[CH:12][CH3:13])[CH2:5][CH2:4][CH:3]=[C:2]([CH3:9])[CH3:1]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 207456-Methyl-5-hepten-2-olHCID 637090Crotonic Acid

생성물 1

HCID 86762531But-2-enoic acid 1,5-dimethyl-hex-4-enyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
121.5 °C

실험 절차

6-Methyl-hept-5-en-2-ol (256 g, commercially available at IFF), crotonic acid (193 g), PTSA (2.5 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 110-133° C. Water was removed azeotropically. The reaction was aged at reflux for about 6 hours until no more water evolved. The reaction mixture was cooled to under 60° C. and quenched with water (300 mL). The aqueous and organic layers were split. The organic layer was subsequently washed with sodium carbonate (2%, 300 mL) and further fractional distilled to provide but-2-enoic acid 1,5-dimethyl-hex-4-enyl ester (204 g) with a boiling point of 98° C. at 4 mmHg.

후처리

  1. customfitted with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. customWater was removed azeotropically
  4. temperatureat reflux for about 6 hours until no more water
  5. temperatureThe reaction mixture was cooled to under 60° C.
  6. customquenched with water (300 mL)
  7. customThe aqueous and organic layers were split
  8. washThe organic layer was subsequently washed with sodium carbonate (2%, 300 mL)
  9. distillationfurther fractional distilled

출처 및 근거

ORD 기록
ord-c672b3be4f6641ce8464626d717c7fad
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785677B1

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