Sulfuric Acid → Isopropyl acetoacetate

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].S(=O)(=O)(O)O.[CH:15](O)(C)C>>[C:1]([O:7][CH:8]([CH3:15])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 3776Isopropanol

HCID 8868Ethyl Acetoacetate

Product 1

HCID 68329Isopropyl acetoacetate

Procedure

A solution of ethyl acetoacetate (250 g.) and concentrated sulphuric acid (10 ml.) in isopropanol (1500 ml.) was heated at reflux for 3 hours. The solvent was removed by distillation, the residue was neutralised by treatment with barium carbonate, filtered and distilled under reduced pressure to give isopropyl acetoacetate (139 g.), b.p. 79°-82° C./20 mm Hg, in the form of a colourless liquid.