p-Toluenesulfonic acid → HCID 86762525, compound

HRID 1627966Notes

Reaction equation

HRID 1627966 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

A reaction flask was charged with ethylmagnesium chloride (CH3CH2MgCl) (2 M, 2.17 L) and cooled to −10° C. Isobutyraldehyde ((CH3)2CHCHO) (295 g) was fed over about 1 hour while the temperature was kept under 15° C. The reaction mixture was aged to room temperature over about 6 hours and then poured into a mixture of ice and acetic acid (293 g). Hexanes (350 mL) were added and aqueous and organic layers were split. The organic layer was separated, washed sequentially with sodium bicarbonate (NaHCO3), brine, and water, and further distilled to provide 2-methyl-pentan-3-ol (336 g). 2-Methyl-pentan-3-ol (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-48cffaee1b1d4c6ea9da2a5fa6d20220
Source dataset
uspto-grants-2014_07
Patent number
US08785677B1

Reaction notes

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