p-Toluenesulfonic acid → HCID 86762525, compound

HRID 1621073Notes

Reaction equation

HRID 1621073 reaction equation
[CH3:1][CH:2]([CH:4]([OH:7])[CH2:5][CH3:6])[CH3:3].[CH3:8][C:9](=[CH:13][CH3:14])[C:10](O)=[O:11].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:5]([CH:4]([O:7][C:10](=[O:11])[C:9]([CH3:8])=[CH:13][CH3:14])[CH:2]([CH3:3])[CH3:1])[CH3:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66562-Butenoic acid, 2-methyl-HCID 112642-Methylpentan-3-ol

Product 1

HCID 86762525HCID 86762525, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

2-Methyl-pentan-3-ol (prepared as above in EXAMPLE I) (153 g), 2-methyl-but-2-enoic acid (100 g), toluene (200 mL), and PTSA (8 g) were charged into to 2-L reaction flask fitted with a Dean-Stark trap. The reaction mixture was heated to reflux at about 120° C. Water was removed. The reaction mixture was aged at reflux for about 13-14 hours till GC analysis showed completion of the reaction. The resulting reaction mixture was washed sequentially with sodium bicarbonate and brine, and further purified by fractional distillation to provide 2-methyl-but-2-enoic acid 1-ethyl-2-methyl-propyl ester (81 g) with a boiling point of 91° C. at 1.1 mmHg.

Workup

  1. customfitted with a Dean-Stark trap
  2. temperatureThe reaction mixture was heated
  3. customWater was removed
  4. temperatureat reflux for about 13-14 hours till GC analysis
  5. customcompletion of the reaction
  6. customThe resulting reaction mixture
  7. washwas washed sequentially with sodium bicarbonate and brine
  8. distillationfurther purified by fractional distillation

Sources & evidence

ORD record
ord-33a25f093d6f4e1da8682db1ece20fad
Source dataset
uspto-grants-2014_07
Patent number
US08772533B1

Reaction notes

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