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

HRID 247533Notes

Reaction equation

HRID 247533 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:23]=[CH:22][C:21]([O-:24])=[C:20]([CH3:25])[CH:19]=1.[Na+]>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

4

Reactant 2

HCID 19765057Diethyl-2-chloro-propionyl-malonateHCID 23678815Phenol, 4-chloro-2-methyl-, sodium salt (1:1)

Product 1

HCID 20159510Diethyl-2-(2'-methyl-4-chloro-phenoxy)-propionyl-malonateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 25.1 g of diethyl-2-chloro-propionyl-malonate, 16.5 g of sodium 4-chloro-2-methyl-phenolate and 100 ml of dimethyl formamide is stirred at 60° C. for 48 hours. The reaction mixture is filtered and the filtrate is evaporated. The residue is dissolved in 100 ml of benzene and washed succesively with 100 ml of a saturated aqueous sodium bicarbonate solution and 100 ml of water. The benzene layer is evaporated to give 28.7 g of the desired compound, yield 82%.

Workup

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

Sources & evidence

ORD record
ord-0ada83dcd91d4eff8387500632291a3c
Source dataset
uspto-grants-1987_11
Patent number
US04708733

Reaction notes

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