Hydrochloric Acid → Ethyl 2-hydroxy-5-cyano-5-phenyl-2,4-pentadienoate

HRID 1074024Notes

Reaction equation

HRID 1074024 reaction equation
Cl.CN(C)[C:4](=[CH:10][CH:11]=[C:12]([C:19]#[N:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([OH:24])C>>[OH:24][C:4](=[CH:10][CH:11]=[C:12]([C:19]#[N:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54027283Ethyl 2-dimethylamino-5-cyano-5-phenyl-2,4-pentadienoate

Product 1

HCID 86743579Ethyl 2-hydroxy-5-cyano-5-phenyl-2,4-pentadienoate

Conditions

Temperature
10 °C

Procedure

1N aqueous hydrochloric acid solution (87 cc) is added in the course of 3 minutes to a solution, maintained under reflux, of ethyl 2-dimethylamino-5-cyano-5-phenyl-2,4-pentadienoate (21.3 g) in ethanol (27 cc). The mixture is cooled to a temperature of approximately 10° C. and the precipitate obtained is filtered off, washed with ethanol (15 cc) and dried. Ethyl 2-hydroxy-5-cyano-5-phenyl-2,4-pentadienoate (12.1 g), m.p. 189° C., is thereby obtained.

Workup

  1. temperaturemaintained
  2. customthe precipitate obtained
  3. filtrationis filtered off
  4. washwashed with ethanol (15 cc)
  5. customdried

Sources & evidence

ORD record
ord-eb9102a5b0814fe7b88dfa7bc871c343
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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