3-Methylpentan-2-ol → HCID 86762558, compound

HRID 1627964Notes

Reaction equation

HRID 1627964 reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[CH:3]([OH:5])[CH3:4].[C:8](O)(=[O:12])/[CH:9]=[CH:10]/[CH3:11]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:4][CH:3]([O:5][C:8](=[O:12])[CH:9]=[CH:10][CH3:11])[CH:2]([CH3:1])[CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 112613-Methylpentan-2-olHCID 637090Crotonic Acid

Product 1

HCID 86762558HCID 86762558, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

3-Methyl-pentan-2-ol (400 g), crotonic acid (CH3CH═CHCOOH) (445.5 g), toluene (400 mL), and para-toluenesulfonic acid (PTSA) (4 g) were charged into to 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a condenser, and 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 for about 3.5 hours. The resulting reaction mixture was then cooled and washed sequentially with water, aqueous sodium hydroxide (NaOH) (10%), and brine. The aqueous and organic layers were split. The organic layer was fractional distilled to provide but-2-enoic acid 1,2-dimethyl-butyl ester (444 g) with a boiling point of 106° C. at 34 mmHg.

Workup

  1. customfitted with a mechanical stirrer
  2. temperatureThe reaction mixture was heated to reflux
  3. customWater was collected
  4. customremoved via the Bidwell-Sterling trap
  5. customThe resulting reaction mixture
  6. temperaturewas then cooled
  7. washwashed sequentially with water, aqueous sodium hydroxide (NaOH) (10%), and brine
  8. customThe aqueous and organic layers were split
  9. distillationThe organic layer was fractional distilled

Sources & evidence

ORD record
ord-423f24f7e46f4fc09600ff296e36c0c4
Source dataset
uspto-grants-2014_07
Patent number
US08785677B1

Reaction notes

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