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

HRID 1709100Notes

Reaction equation

HRID 1709100 reaction equation
[Cl-].[Mg+2].[Cl-].[C:4]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl:15][C:16]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:17]=1[O:18][C:19]1[CH:30]=[CH:29][C:22]([O:23][CH:24]([CH3:28])[C:25](Cl)=[O:26])=[CH:21][CH:20]=1.Cl>C(N(CC)CC)C.C(#N)C>[CH2:13]([O:12][C:4](=[O:11])[CH:5]([C:25](=[O:26])[CH:24]([O:23][C:22]1[CH:29]=[CH:30][C:19]([O:18][C:17]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:16]=2[Cl:15])=[CH:20][CH:21]=1)[CH3:28])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360315Magnesium ChlorideHCID 129429952-[4-(2,4-Dichlorophenoxy)phenoxy]propanoyl chloride

Product 1

HCID 23037017Diethyl-2-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-propionyl-malonateYield 89.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Into a 500 ml flask equipped with a stirrer and a dropping funnel 9.52 g of anhydrous magnesium chloride and 100 ml of anhydrous acetonitrile are introduced. To the heterogeneous mixture 16.0 g of diethyl malonate are added, the reaction flask is placed into an ice bath whereupon 28 ml of triethyl amine are added. To the solution at 0° C. 35 g of 2-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-propionyl-chloride are added dropwise within 15 minutes. The reaction mixture is stirred at 0° C. for an hour and at room temperature for 12 hours whereupon it is cooled to 0° C. and 60 ml of a 5M hydrochloric acid solution are added. The solution thus obtained is extracted three times with 100 ml of ether each, the united extracts are dried over magnesium sulfate and the solvent and the traces of diethyl malonate are removed. The slightly yellow oil thus obtained slowly solidifies. Thus 41.8 g of the desired compound are obtained, yield 89%, mp.: 46°-50° C.

Workup

  1. additionare introduced
  2. additionare added
  3. customat 0° C
  4. temperatureis cooled to 0° C.
  5. customThe solution thus obtained
  6. extractionis extracted three times with 100 ml of ether each, the united extracts
  7. dry with materialare dried over magnesium sulfate
  8. customthe solvent and the traces of diethyl malonate are removed
  9. customThe slightly yellow oil thus obtained slowly

Sources & evidence

ORD record
ord-8350684f36af4592acae27b815095940
Source dataset
uspto-grants-1990_08
Patent number
US04948420

Reaction notes

Loading…