Isopropyl chloroacetate → Diisopropyl malonate

HRID 326005

Reaction equation

HRID 326005 reaction equation
[CH:1]([O:4][C:5](=[O:8])[CH2:6]Cl)([CH3:3])[CH3:2].[OH-:9].[Na+]>C(O)(C)C>[CH:1]([O:4][C:5](=[O:8])[CH2:6][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:9])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7759Isopropyl chloroacetateHCID 14798Sodium Hydroxide

Product 1

HCID 83223Diisopropyl malonateYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

20 g of Co2 (CO)8 in 2.5 liters of isopropanol and 546 g (4 moles) of chloroacetic acid isopropyl ester are placed in a pressure vessel of a capacity of 18 liters, as in Example 1. At 55° C., and a pressure of 5 bars of CO, a 2.93% solution of sodium hydroxide in isopropanol is pumped into the vessel over a period of 3 hours, maintaining a pH of 7.0. At a transformation of 82%, 615 g of malonic acid diisopropyl ester (92% yield) is obtained after the usual processing. 98 g of chloroacetic acid isopropyl ester is recovered.

Workup

  1. temperaturemaintaining a pH of 7.0

Sources & evidence

ORD record
ord-ffe40bfa903a41ce950ae81b27983251
Source dataset
uspto-grants-1984_04
Patent number
US04443624

Linked notes

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