3-Methyl-2-butanol → But-2-enoic acid 1,2-dimethyl-propyl ester

HRID 1627965Notes

Reaction equation

HRID 1627965 reaction equation
[CH3:1][CH:2]([CH3:6])[CH:3]([OH:5])[CH3:4].[C:7](O)(=[O:11])/[CH:8]=[CH:9]/[CH3:10]>CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:4][CH:3]([O:5][C:7](=[O:11])[CH:8]=[CH:9][CH3:10])[CH:2]([CH3:6])[CH3:1]

Participants

5

Reactant 2

HCID 117323-Methyl-2-butanolHCID 637090Crotonic Acid

Product 1

HCID 86762524But-2-enoic acid 1,2-dimethyl-propyl esterYield 52.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

3-Methyl-butan-2-ol (180 g), crotonic acid (165 g), toluene (200 mL), and PTSA (8 g) were charged into to a 2-L reaction flask fitted with a Bidwell-Sterling trap. The reaction mixture was heated to reflux. Water was collected and removed via the Bidwell-Sterling trap. The reaction mixture was aged at reflux for about 13-15 hours till GC analysis showed completion of the reaction. The resulting reaction mixture was washed sequentially with brine, sodium carbonate (Na2CO3), and brine, and further purified by fractional distillation to provide but-2-enoic acid 1,2-dimethyl-propyl ester (157 g) with a boiling point of 53° C. at 0.77 mmHg.

Workup

  1. customfitted with a Bidwell-Sterling trap
  2. temperatureThe reaction mixture was heated to reflux
  3. customWater was collected
  4. customremoved via the Bidwell-Sterling trap
  5. temperatureat reflux for about 13-15 hours till GC analysis
  6. customcompletion of the reaction
  7. customThe resulting reaction mixture
  8. washwas washed sequentially with brine, sodium carbonate (Na2CO3), and brine
  9. distillationfurther purified by fractional distillation

Sources & evidence

ORD record
ord-200718d37ff94ed09f3f299573fda685
Source dataset
uspto-grants-2014_07
Patent number
US08785677B1

Reaction notes

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