Ethanol → Diethyl Malonate

HRID 326000Notes

Reaction equation

HRID 326000 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5][Cl:6])[CH3:2].[CH3:8][CH2:9][O-:10].[Na+].[CH2:12]([OH:14])C>>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][C:12]([O:10][CH2:9][CH3:8])=[O:14])[CH3:2].[CH2:1]([O:3][C:4](=[O:7])[CH2:5][Cl:6])[CH3:2].[CH2:1]([O:3][C:4](=[O:7])[CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 7751Ethyl chloroacetateHCID 2723922Sodium ethoxide

Product 3

HCID 7751Ethyl chloroacetateHCID 7761Diethyl MalonateYield 95%HCID 8857Ethyl AcetateYield 1.6%

Procedure

As in Example 1, but at 7.5 at. CO and a pH of 6.0, 490 g (4 moles) of chloroacetic acid ethyl ester is reacted with 1.38 kg of 15.8% sodium ethylate (3.2 moles) in ethanol, for 6 hours. Processing the reaction mixture yields 490 g of malonic acid diethyl ester (95% yield), 4.4 g of acetic acid ethyl ester (1.6% yield), 5.9 g of residue, and 98 g of chloroacetic acid ethyl ester.

Sources & evidence

ORD record
ord-771530ff216541469138fc54fff9d588
Source dataset
uspto-grants-1984_04
Patent number
US04443624

Reaction notes

Loading…