Hydrochloric Acid → HCID 20513478, compound

HRID 1164037Notes

Reaction equation

HRID 1164037 reaction equation
C([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:12]=1[O:25][CH3:26])([CH2:9][CH3:10])[C:4]([O:6]CC)=[O:5])#N.Cl>C(O)(=O)C>[CH3:26][O:25][C:12]1[C:13]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[CH:14][CH:15]=[CH:16][C:11]=1[CH:3]([CH2:9][CH3:10])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20513453HCID 20513453, compound

Product 1

HCID 20513478HCID 20513478, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]butyrate (4.1 g), conc. hydrochloric acid (20 ml) and acetic acid (40 ml) was refluxed under heating for 48 hours. The reaction mixture was evaporated, and 10% aqueous sodium hydroxide and ethanol were added to the residue. The mixture was refluxed under heating for 30 minutes and then evaporated. Water was added to the residue, washed with diethyl ether, acidified with conc. hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried and evaporated to give oily 2-[2-methoxy-3-(o-tolyloxy)phenyl]butyric acid (2.2 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 48 hours
  3. customThe reaction mixture was evaporated
  4. addition10% aqueous sodium hydroxide and ethanol were added to the residue
  5. temperatureThe mixture was refluxed
  6. temperatureunder heating for 30 minutes
  7. customevaporated
  8. additionWater was added to the residue
  9. washwashed with diethyl ether
  10. extractionextracted with diethyl ether
  11. washThe extract was washed with water
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-ac58b0f4cdc84df8b56a8932bd322b36
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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