Potassium Carbonate → Diethyl-2-(2'-methyl-4-chloro-phenoxy)-propionyl-malonate

HRID 247532Notes

Reaction equation

HRID 247532 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:11](=[O:15])[CH:12](Cl)[CH3:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([CH3:25])[C:21]([OH:24])=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:11](=[O:15])[CH:12]([O:24][C:21]1[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][C:20]=1[CH3:25])[CH3:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 148554-Chloro-2-methylphenolHCID 19765057Diethyl-2-chloro-propionyl-malonate

Product 1

HCID 20159510Diethyl-2-(2'-methyl-4-chloro-phenoxy)-propionyl-malonateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.1 g of diethyl-2-chloro-propionyl-malonate and 14.2 g of 4-chloro-o-cresol are dissolved in 100 ml dimethyl formamide. The mixture is stirred at 60° C. for 48 hours in the presence of 13.8 g of potassium carbonate. 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 bicarbonate solution and 100 ml of water. The benzene phase is evaporated to yield 28 g of the desired compound, yield 80%.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in 100 ml of benzene
  4. washwashed successively with 100 ml of a saturated aqueous sodium bicarbonate solution and 100 ml of water
  5. customThe benzene phase is evaporated

Sources & evidence

ORD record
ord-2174e0666d7c4915a1fae1d06fd1d4a2
Source dataset
uspto-grants-1987_11
Patent number
US04708733

Reaction notes

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