Dimethyl malonate → Dimethyl-4-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-2-pentenoyl-malonate

HRID 35148Notes

Reaction equation

HRID 35148 reaction equation
[Na].[C:2]([O:9][CH3:10])(=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Cl:11][C:12]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:13]=1[O:14][C:15]1[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[CH:21]=[CH:22][C:23](Cl)=[O:24])=[CH:17][CH:16]=1>CCOCC>[CH3:7][O:6][C:4](=[O:5])[CH:3]([C:23](=[O:24])[CH:22]=[CH:21][CH:20]([O:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][C:13]2[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:12]=2[Cl:11])=[CH:28][CH:27]=1)[CH3:26])[C:2]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 5360545SodiumHCID 569848544-[4-(2,4-Dichlorophenoxy)phenoxy]pent-2-enoyl chloride

Product 1

HCID 57036708Dimethyl-4-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-2-pentenoyl-malonateYield 79.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

From 4.6 g of sodium, 26 g of dimethyl malonate and 60 ml of ether a dimethyl sodium malonate solution is prepared which is added dropwise under stirring to a mixture of 37 g of 4-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-2-pentenoyl chloride and 50 ml of ether. The reaction mixture is heated to boiling for 2 hours and worked up as described in Example 1. Thus 37 g of the faint yellow crystalline desired compound are obtained, yield 79%, mp.: 60°-63° C.

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is heated

Sources & evidence

ORD record
ord-29de5aef3cae4a3189a7dafacb2080ee
Source dataset
uspto-grants-1988_08
Patent number
US04765825

Reaction notes

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