Formaldehyde → 1,3-Diethyl 2-oxopropanedioate

HRID 622169Notes

Reaction equation

HRID 622169 reaction equation
C=[C:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C=O.[O:15]=[O+][O-]>CO.[Pd]>[C:8]([O:10][CH2:11][CH3:12])(=[O:9])[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:15]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 24823OzoneHCID 951181,3-Diethyl 2-methylenepropanedioate

Product 1

HCID 691051,3-Diethyl 2-oxopropanedioateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

258 g of diethyl methylenemalonate, prepared by a Knoevenagel condensation of malonic ester and formaldehyde, are dissolved in 1 liter of methanol and reacted with ozone, and subsequently hydrogenated, analogously to the procedure indicated in Example 5. 5 g of 10% Pd-on-C in 200 ml of methanol are initially taken as the hydrogenation catalyst. The consumption of hydrogen is 28.9 standard liters (86% of theory). Working up as in Example 5 and rectification in vacuo gives 214 g of diethyl mesoxalate boiling at 110°-112° C./20, corresponding to a yield of 82% of theory.

Workup

  1. customThe consumption of hydrogen

Sources & evidence

ORD record
ord-1cd0b6c1303c4ad6ab6cf351825feca5
Source dataset
uspto-grants-1988_09
Patent number
US04769464

Reaction notes

Loading…