Allyl chloride → Diallyl malonate

HRID 1700836

Reaction equation

HRID 1700836 reaction equation
[CH2:1](Cl)[CH:2]=[CH2:3].[C:5]([O-:11])(=[O:10])[CH2:6][C:7]([O-:9])=[O:8].[Na+].[Na+].Cl[C:15]1[CH:20]=CC=C[CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:5]([O:11][CH2:20][CH:15]=[CH2:16])(=[O:10])[CH2:6][C:7]([O:9][CH2:1][CH:2]=[CH2:3])=[O:8]

Participants

6

Reactant 3

HCID 7850Allyl chlorideHCID 7964ChlorobenzeneHCID 8865Malonic acid, disodium salt

Product 1

HCID 228227Diallyl malonateYield 16%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In an autoclave, 7.65 g (0.1 mol) of allyl chloride were added to a solution of 2.96 g (20 mmol) of disodium malonate and 0.64 g (2 mmol) of tetrabutylammonium bromide in 5 ml of water and 10 ml of chlorobenzene. The mixture was heated to 100° C. over a period of 30 minutes, with the pressure in the autoclave rising to 2.5 bar. After a reaction time of 3½ hours at 100° C., the mixture was cooled to room temperature and depressurized. The aqueous phase was extracted with tert-butyl methyl ether (2×5 ml). The combined organic phases were dried over sodium sulfate and analyzed by gas chromatography (internal standard: dimethyl succinate). The product yield was 16 percent.

Workup

  1. temperatureAfter a reaction time of 3½ hours at 100° C., the mixture was cooled to room temperature
  2. extractionThe aqueous phase was extracted with tert-butyl methyl ether (2×5 ml)
  3. dry with materialThe combined organic phases were dried over sodium sulfate

Sources & evidence

ORD record
ord-b57fe02393d84ac1b47f8c7cdcf0b734
Source dataset
uspto-grants-2002_02
Patent number
US06350898B1

Linked notes

Loading…