Hydrochloric Acid → HCID 20513459, compound

HRID 1164028Notes

Reaction equation

HRID 1164028 reaction equation
[C:1]([C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:11]=1[O:24][CH3:25])(C)[C:4]([O:6]CC)=[O:5])#N.Cl>C(O)(=O)C>[CH3:25][O:24][C:11]1[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][CH:14]=[CH:15][C:10]=1[CH:3]([CH3:1])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20513476HCID 20513476, compound

Product 1

HCID 20513459HCID 20513459, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(2-chlorophenoxy)phenyl]propionate (5.8 g), conc. hydrochloric acid (20 ml) and acetic acid (40 ml) was refluxed under heating for 26 hours. After cooling, the reaction mixture was evaporated, and water was added to the residue. The mixture was evaporated again, and the oily residue was dissolved in saturated aqueous sodium bicarbonate under warming. After cooling, the aqueous solution was washed with diethyl ether, acidified with conc. hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried and then evaporated to give oily 2-[2-methoxy-3-(2-chlorophenoxy)phenyl]propionic acid (2.7 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 26 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated
  5. additionwater was added to the residue
  6. customThe mixture was evaporated again
  7. dissolutionthe oily residue was dissolved in saturated aqueous sodium bicarbonate
  8. temperatureunder warming
  9. temperatureAfter cooling
  10. washthe aqueous solution was washed with diethyl ether
  11. extractionextracted with diethyl ether
  12. washThe extract was washed with water
  13. customdried
  14. customevaporated

Sources & evidence

ORD record
ord-6e69e43190c348ad8935d91c06437d5a
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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