Diethyl-2-chloro-propionyl-malonate → Diethyl-2-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-propionyl-malonate

HRID 1709101Notes

Reaction equation

[Na].[Cl:2][C:3]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([O-:12])=[CH:8][CH:7]=1.[CH2:18]([O:20][C:21](=[O:33])[CH:22]([C:28](=[O:32])[CH:29](Cl)[CH3:30])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:19]>CS(C)=O>[CH2:26]([O:25][C:23](=[O:24])[CH:22]([C:28](=[O:32])[CH:29]([O:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][C:4]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:3]=2[Cl:2])=[CH:11][CH:10]=1)[CH3:30])[C:21]([O:20][CH2:18][CH3:19])=[O:33])[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

27.7 g of sodium-4-(2',4'-dichloro-phenoxy)-phenolate and 25.1 g of diethyl-2-chloro-propionyl-malonate are dissolved in 150 ml of dimethyl sulfoxide and the reaction mixture is stirred at 60° C. for 48 hours under stirring. The reaction mixture is filtered and the filtrate is evaporated. The residue is dissolved in 100 ml of benzene and washed successively with 100 ml of a saturated aqueous sodium hydrogen carbonate solution and water. The benzene solution is evaporated. Thus 30 g of the desired compound are obtained, yield 61%.

Workup

stirringunder stirring
filtrationThe reaction mixture is filtered
customthe filtrate is evaporated
dissolutionThe residue is dissolved in 100 ml of benzene
washwashed successively with 100 ml of a saturated aqueous sodium hydrogen carbonate solution and water
customThe benzene solution is evaporated

Sources & evidence

ORD record: ord-41bffb4b3a5a4b44a31d7fde63e87897
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948420

Reaction notes

Loading…