1-Octanol → Octyl 2-butenoate

HRID 1621080Notes

Reaction equation

HRID 1621080 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[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>[CH2:1]([O:9][C:10](=[O:14])[CH:11]=[CH:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 9571-OctanolHCID 637090Crotonic Acid

Product 1

HCID 90848Octyl 2-butenoateYield 81.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

Octan-1-ol (221 g), crotonic acid (194 g), PTSA (6.4 g), and toluene (300 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 7-8 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 fractional distilled to provide but-2-enoic acid octyl ester (273 g) with a boiling point of 123° C. at 11 mmHg.

Workup

  1. customfitted with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. customWater was removed azeotropically
  4. temperatureat reflux for about 7-8 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 fractional distilled

Sources & evidence

ORD record
ord-30d13191e9344da0ba3fe8d3d57de376
Source dataset
uspto-grants-2014_07
Patent number
US08772533B1

Reaction notes

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