Hydrochloric Acid → Diethyl 2-hydroxy-5-(3-phenoxybenzylthio)-2,4-hexadienedioate

HRID 477334Notes

Reaction equation

HRID 477334 reaction equation
CN(C)[C:3](=[CH:9][CH:10]=[C:11]([S:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.C([OH:36])C>>[OH:36][C:3](=[CH:9][CH:10]=[C:11]([S:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54232051HCID 54232051, compound

Product 1

HCID 86743589Diethyl 2-hydroxy-5-(3-phenoxybenzylthio)-2,4-hexadienedioate

Conditions

Temperature
20 °C

Procedure

The procedure is as in Example 2, starting with diethyl 2-dimethylamino-5-(3-phenoxybenzylthio)-2,4-hexadienedioate (7 g), 12N aqueous hydrochloric acid solution (23 cc) and ethanol (46 cc). The mixture is heated to boiling for 1 minute, and is then cooled to a temperature of approximately 20° C. After purification by chromatography on a silica column with dichloromethane as eluent, diethyl 2-hydroxy-5-(3-phenoxybenzylthio)-2,4-hexadienedioate (4.5 g) is obtained in the form of a yellow oil (Rf=0.2; thin layer chromatography on silica gel; eluent: dichloromethane).

Workup

  1. temperatureThe mixture is heated
  2. customAfter purification by chromatography on a silica column with dichloromethane as eluent

Sources & evidence

ORD record
ord-7f3e1dfb44f54688bd59e656d09f991a
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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