Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]cinnamic acid
Reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:15]([C:17]3[CH:29]=[CH:28][C:20]([CH:21]=[CH:22][C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2.O.[OH-].[Li+].Cl>CO.COCCOC.O>[CH3:1][C:2]1([CH3:30])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([NH:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[CH:28][CH:29]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The above ester (109 mg, 0.269 mmol) was dissolved in methanol-DME-water (3:2:1, 4.2 ml), the solution was added with lithium hydroxide monohydrate (LiOH.H2O, 15 mg, 0.357 mmol), and the mixture was refluxed by heating for 1 hour. The mixture was cooled on ice, and then added with aqueous hydrochloric acid (1 N, 0.36 ml, 0.36 mmol), and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The residue was recrystallized to obtain the title compound (96 mg, 95%) as colorless prisms.
Workup
- temperaturethe mixture was refluxed
- temperatureby heating for 1 hour
- temperatureThe mixture was cooled on ice
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated
- customThe residue was recrystallized
Sources & evidence
- ORD record
- ord-d2874e70987b41929b8b2d95f149df24
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633335B2
Reaction notes
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