Sodium Chloride → Ethyl 3-(chloro-4-cyanophenyl)propanoate

HRID 67866Notes

Reaction equation

HRID 67866 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:3]=1[CH2:4][CH:5](C(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:3]=1[CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 13042094HCID 13042094, compound

Product 1

HCID 13042095Ethyl 3-(chloro-4-cyanophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
135 °C

Procedure

A mixture of diethyl 2-(2-chloro-4-cyanobenzyl)malonate (9.0 g, 0.03 mol), sodium chloride (2.12 g, 0.04 mol), and water (0.86 g 0.05 mol) in 30 mL of DMSO was heated to 135° C. and then the temperature was gradually raised to 170° C. over a 3 h period. The mixture was diluted with water and extracted with ether. Evaporation and distillation gave ethyl 3-(2-chloro-4-cyanophenyl)propanoate as an oil: 5.8 g; bp 138°-140° C. (0.1 mm Hg) Anal. calcd for C12H12ClNO2 : C, 60.64; H, 5.09; N, 5.89. Found: C, 60.48; H, 5.08; N, 5.84. ##STR29##

Workup

  1. temperaturethe temperature was gradually raised to 170° C. over a 3 h period
  2. extractionextracted with ether
  3. customEvaporation and distillation

Sources & evidence

ORD record
ord-b952d216b39d4402be7ddeea2d746970
Source dataset
uspto-grants-1982_08
Patent number
US04347177

Reaction notes

Loading…