Toluene → (E)-tert-Butyl hept-2-enoate

HRID 635643

Reaction equation

HRID 635643 reaction equation
[C:1]([OH:9])(=[O:8])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH3:7].[C:10]1([CH3:16])[CH:15]=CC=C[CH:11]=1>>[C:1]([O:9][C:10]([CH3:16])([CH3:15])[CH3:11])(=[O:8])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 1140TolueneHCID 52827092-Heptenoic acid

Product 1

HCID 15636290(E)-tert-Butyl hept-2-enoate

Procedure

74.79 ml (312 mmol) of 1,2-(di-tert-butyl)trimethylamine were added to a stirred mixture of 5 g (39 mmol) of (E)-2-heptenoic acid in 100 ml of toluene at 80° C. The mixture was stirred under reflux for 30 minutes and then cooled to room temperature. The mixture was washed in sequence with water and saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulphate and filtered. The solvent was removed by evaporation. There were obtained 7.5 g of tert-butyl (E)-2-heptenoate as a yellow oil; MS: m/e 185.0 [M+H].

Workup

  1. temperatureunder reflux for 30 minutes
  2. washThe mixture was washed in sequence with water and saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-9780b1716e3747bd9ff011df2d496175
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Linked notes

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