Methyl Acrylate → 4-Acetylbutyric acid

HRID 1486521Notes

Reaction equation

HRID 1486521 reaction equation
[O:1]=[C:2](C)[CH2:3]CC(OCC)=O.BrBr.[C:13]([O:19]CC)(=[O:18])[CH2:14][C:15]([CH3:17])=O.C(OC)(=O)C=C>C(O)(=O)C>[O:1]=[C:2]([CH3:3])[CH2:17][CH2:15][CH2:14][C:13]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 8868Ethyl AcetoacetateHCID 10883Ethyl levulinateHCID 24408Bromine

Product 1

HCID 184074-Acetylbutyric acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Appropriate α-bromoketone 21b was prepared by bromination of ethyl 4-oxopentanoate by bromine in acetic acid. α-bromoketone 21c was prepared according to literature (Lugtenburg J. et. al., Eur. J. Org. Chem. 2002, 189-2202) from ethyl acetoacetate and methyl acrylate in 1,4-addition reaction and subsequent decarboxylation under acidic conditions to give 5-oxohexanoic acid. Esterification and bromination gave α-bromoketone 21c (methyl 6-bromo-5-oxohexanoic acid) in 4 step procedure. α-Chloroketone 21a

Sources & evidence

ORD record
ord-482773f858684b28888d48e7f57327fa
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

Loading…