Crotonic Acid → HCID 86762527, compound

HRID 1627969Notes

Reaction equation

HRID 1627969 reaction equation
[CH3:1][CH:2]([CH:7]([CH3:9])[CH3:8])[CH2:3][CH:4]([OH:6])[CH3:5].[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>[CH3:5][CH:4]([O:6][C:10](=[O:14])[CH:11]=[CH:12][CH3:13])[CH2:3][CH:2]([CH3:1])[CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 637090Crotonic AcidHCID 53749111HCID 53749111, compound

Product 1

HCID 86762527HCID 86762527, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

The obtained 4,5-dimethyl-hexan-2-ol (296 g), crotonic acid (391 g,), PTSA (3 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 4-5 hours until no more water evolved. The reaction 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 1,3,4-trimethyl-pentyl ester (241 g) with a boiling point of 108° C. at 13 mmHg.

Workup

  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 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-21499c2bb4de4065972ce2899cede5d9
Source dataset
uspto-grants-2014_07
Patent number
US08785677B1

Reaction notes

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