Hydrochloric Acid → HCID 10420872, compound
Reaction equation
C([O:3][C:4](=[O:18])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[CH:14][CH2:15][CH2:16][CH3:17])C.[OH-].[K+].Cl>CO.C(OCC)(=O)C>[CH:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:6]=[CH:5][C:4]([OH:18])=[O:3])=[CH:14][CH2:15][CH2:16][CH3:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of (E)-3-[2-((Z)-1-pentenyl)phenyl]propenoic acid ethyl ester (2 g) in 20% aqueous methanol was added potassium hydroxide (2.3 g). The mixture was stirred for 2 hours at 60° C., adjusted to pH 1 with hydrochloric acid and extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the solvent was evaporated. The residue was dissolved in a mixture of n-hexane and ethyl acetate (4:1). The solution was added to dicyclohexylamine (1.63 ml) to give crystals. The crystals were dissolved in ethyl acetate and washed with 1N sulfuric acid. The solution was dried over magnesium sulfate, filtered and evaporated to give (E)-3-[2-((Z)-1-pentenyl)phenyl]propenoic acid (0.92 g).
Workup
- extractionextracted with ethyl acetate
- dry with materialAfter the extract was dried over magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in a mixture of n-hexane and ethyl acetate (4:1)
- additionThe solution was added to dicyclohexylamine (1.63 ml)
- customto give crystals
- washwashed with 1N sulfuric acid
- dry with materialThe solution was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-8510743973a84d3084e1b251001c38e4
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05436140
Reaction notes
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