Ethanol → Ethyl chloroacetate

HRID 434788Notes

Reaction equation

HRID 434788 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]

Participants

5

Reactant 3

HCID 702EthanolHCID 7751Ethyl chloroacetateHCID 2723922Sodium ethoxide

Product 2

HCID 7751Ethyl chloroacetateHCID 7761Diethyl Malonate

Procedure

As in Example 1, but in a pressure vessel with a capacity of 18 liters equipped with a pH measuring system, 3.06 kg (25 moles) of chloroacetic acid ethyl ester, 1 liter of ethanol and 125 g of Co2 (CO)8 are combined at 5 at. CO. At a reaction temperature of 55° C., 7.03 kg of 21.9% sodium ethylate (22.6 moles) is pumped in over a period of 51/2 hours, at a pH of 7.0. 3.43 kg of malonic acid diethyl ester is obtained (yield 95%) plus 290 g of chloroacetic acid ethyl ester.

Workup

  1. customAs in Example 1, but in a pressure vessel with a capacity of 18 liters equipped with a pH

Sources & evidence

ORD record
ord-017971bb1d6b4316849911b88a45e747
Source dataset
uspto-grants-1983_08
Patent number
US04399300

Reaction notes

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