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

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

Reactant 3

HCID 1118Sulfuric Acid

HCID 3776Isopropanol

HCID 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

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

Sources & evidence

ORD record: ord-0db0de5db94641a48e202ca03664dc84
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993694B2

Reaction notes

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