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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 649343Generated: October 30, 2026

Pinacolone → methyl 5,5-dimethyl-2,4-dioxohexanoate

https://huagongshe.com/reaction/649343

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPinacoloneHCID 6416—
ReactantChlorobenzeneHCID 7964—
ReactantDimethyl oxalateHCID 11120—
ReactantSodium MethoxideHCID 10942334—
SolventMethanolHCID 887—
Productmethyl 5,5-dimethyl-2,4-dioxohexanoateHCID 4016750—

Reaction Conditions

Temperature10 °C

Reaction Steps

198 g of methanolic sodium methyate solution (30% strength by weight) are added to 400 g of chlorobenzene. The methanol is distilled off at 65° C. in the course of 1 hour. The mixture is cooled to 10° C. and 118 g (1 mol) of molten oxalic acid dimethyl ester are introduced in the course of 1 hour. Thereafter, 100 g (1 mol) of pinacolin are allowed to run in and the mixture is subsequently stirred at room temperature for 15 minutes. It is heated, and the methanol formed in the reaction is distilled off in the course of 2 hours. Neutralisation with sulphuric acid, separation of the phases and distillation of the organic phase gives 165 g of pivaloylpyruvic acid methyl ester (87.8% of the theoretical yield). Purity: 99.0%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04739104
Source datasetuspto-grants-1988_04
ORD IDord-c677b96512394f8aad7c3b4cc269a35a
Source noteuspto-grants-1988_04