Benzoyl chloride → Diethyl Malonate

HRID 66244Notes

Reaction equation

HRID 66244 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5](N=C(C1C=CC=CC=1)C1C=C(Cl)C=CC=1O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(Cl)(=O)C1C=CC=CC=1>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 136388409[(5-Chloro-2-hydroxy-alpha-phenylbenzyliden)amino] malonic acid diethyl ester

Product 1

HCID 7761Diethyl Malonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7.8 g. of [(5-chloro-2-hydroxy-α-phenylbenzyliden)amino] malonic acid diethyl ester in 15 ml. of pyridine is treated at 10°-15° C. with 3.5 ml. of benzoyl chloride. The mixture is stirred at room temperature for 1 hour and then poured on to 150 ml. of ice-water. The separated oily product is extracted with ether and the organic phase washed with water, then with 2-N sodium carbonate solution and finally with water. After drying over sodium sulfate and evaporation of the solvent, the oily residue is triturated with hexane, crystallization setting in. There is obtained [(2-benzoylloxy-5-chloro-α-phenylbenzyliden)amino] malonic acid diethyl ester in the form of colorless crystals, having a melting point of 108°-110° C. Recrystallization from ethanol increases the melting point to 109°-111° C.

Workup

  1. additionpoured on to 150 ml
  2. extractionThe separated oily product is extracted with ether
  3. washthe organic phase washed with water
  4. dry with materialAfter drying over sodium sulfate and evaporation of the solvent
  5. customthe oily residue is triturated with hexane, crystallization setting in

Sources & evidence

ORD record
ord-3b974cd4468248e399c7808fe8faec64
Source dataset
uspto-grants-1978_12
Patent number
US04130717

Reaction notes

Loading…