Sulfuric Acid → 1-Methylethyl (2E)-2-butenoate

HRID 881776Notes

Reaction equation

HRID 881776 reaction equation
[C:1]([OH:6])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH3:7][CH:8](O)[CH3:9].S(=O)(=O)(O)O>>[CH:8]([O:5][C:1](=[O:6])/[CH:2]=[CH:3]/[CH3:4])([CH3:9])[CH3:7]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 637090Crotonic Acid

Product 1

HCID 53543591-Methylethyl (2E)-2-butenoateYield 76.3%

Procedure

Crotonic acid (193.7 g, 2.25 mol) was dissolved in 2-propanol (860 mL, 11.25 mol) in a 2 L flask and then well stirred, after which sulfuric acid (24 mL, 0.45 mol) was slowly added in droplets to the mixture and refluxed and stirred for 48 hours or longer. The stirred mixture was cooled to room temperature, after which the obtained mixture was washed with distilled water (1000 mL), and the organic layer was separated, neutralized and subjected to atmospheric distillation (80° C.), thus obtaining 220 g (1.71 mol, yield 76.3%) of crotonic acid isopropyl ester.

Workup

  1. temperaturerefluxed
  2. stirringstirred for 48 hours or longer
  3. washafter which the obtained mixture was washed with distilled water (1000 mL)
  4. customthe organic layer was separated
  5. distillationsubjected to atmospheric distillation (80° C.)

Sources & evidence

ORD record
ord-0db0de5db94641a48e202ca03664dc84
Source dataset
uspto-grants-2015_03
Patent number
US08993694B2

Reaction notes

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