Hydrochloric Acid → HCID 19985594, compound

HRID 974186Notes

Reaction equation

HRID 974186 reaction equation
[CH3:1]/[C:2](/[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:17][CH:16]=1)=[CH:3]\[C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][CH:5]=1.[OH-].[K+].Cl>C(O)C.O.CCOCC>[CH3:1]/[C:2](/[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:19][CH:20]=1)=[CH:3]\[C:4]1[CH:14]=[CH:13][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15096743HCID 15096743, compound

Product 1

HCID 19985594HCID 19985594, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 100 mg of ethyl 4-(E-2-methyl-2-(4-(3-methyl-2-butenoxy)phenyl)ethenyl)benzoate in 3 ml of ethanol under argon is added dropwise a solution of 50 mg of potassium hydroxide in 3 ml of ethanol and 1 ml of water. The mixture is stirred at room temperature for 18 hours, cooled and acidified with 3N hydrochloric acid. The resulting precipitate is dissolved in ether, the ether solution washed with saturated aqueous sodium chloride and concentrated to give a solid which is recrystallized from aqueous methanol to give 4-(E-2-methyl-2-(4-(3-methyl-2-butenoxy)phenyl)ethenyl)benzoic acid.

Workup

  1. temperaturecooled
  2. washthe ether solution washed with saturated aqueous sodium chloride
  3. concentrationconcentrated
  4. customto give a solid which
  5. customis recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-919a43f5093a429996d16487529d4ffe
Source dataset
uspto-grants-1991_11
Patent number
US05068252

Reaction notes

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