Fenoprop → Diethyl-2-(2',4',5'-trichloro-phenoxy)-propionyl-malonate

HRID 247534Notes

Reaction equation

[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([OH:8])=O.C(Cl)(=O)C(C)(C)C.C([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C.[C:38]([O:46][CH2:47][CH3:48])(=[O:45])[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>>[CH2:43]([O:42][C:40](=[O:41])[CH:39]([C:6](=[O:8])[CH:5]([O:4][C:3]1[CH:10]=[C:11]([Cl:15])[C:12]([Cl:14])=[CH:13][C:2]=1[Cl:1])[CH3:9])[C:38]([O:46][CH2:47][CH3:48])=[O:45])[CH3:44]

Participants

Reactant 3

HCID 7158Fenoprop

HCID 7761Diethyl Malonate

HCID 62493Pivaloyl chloride

Product 1

HCID 14819487Diethyl-2-(2',4',5'-trichloro-phenoxy)-propionyl-malonateYield 91%

Procedure

One proceeds in an analogous manner to Example 4 except that 27 g of 2-(2',4',5'-trichloro-phenoxy)-propionic acid are reacted first with 12 g of pivaloyl chloride and thereafter with diethyl-ethoxy-magnesium malonate prepared from 17.6 g of diethyl malonate. The reaction mixture is worked up. Thus 37 g of the desired compound are obtained in the form of pale yellow crystals, yield 91%, mp.: 62°-66° C.

Sources & evidence

ORD record: ord-2d6321e7fd9a4ae7bfc10ab15c240d94
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04708733

Reaction notes

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