Methyl acetoacetate → Diethyl methylmalonate

HRID 1285289Notes

Reaction equation

[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12](OC)(=O)CC(C)=O>>[CH3:12][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

Reactant 2

HCID 7757Methyl acetoacetate

HCID 7761Diethyl Malonate

Product 1

HCID 11857Diethyl methylmalonateYield 90%

Procedure

The procedure followed is as in Example 2, but 230.4 g (1.44 mol) of diethyl malonate are pumped in instead of the methyl acetoacetate. After analogous working up, 230.0 g of 90% pure diethyl methylmalonate are obtained on distillation. This corresponds to a yield of 82.6% of the theoretical yield, based on the diethyl malonate employed. The distillate also contains 9.3% of diethyl methoxymethylmalonate as a by-product. A residue of 3.1 g remains in the distillation flask.

Sources & evidence

ORD record: ord-ee8022e0486d4b75a454ea267424ef6a
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567004

Reaction notes

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