Water → HCID 11424320, compound
Reaction equation
C[C:2]([O:15][CH3:16])([C:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])[C:3]([OH:5])=[O:4].O.O.[OH-].[Li+]>CO.O1CCCC1>[CH3:16][O:15][CH:2]([C:6]([CH3:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])[C:3]([OH:5])=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
According to General Procedure II, methyl 2-methoxy-3-methyl-3-phenylbutanoic acid (0.49 g, 2.2 mmol, from Reference Example 38) is dissolved in methanol (10 mL) and tetrahydrofuran (10 mL). To this solution is added water (5 mL) and lithium hydroxide monohydrate (0.18 g, 4.4 mmol), and the resulting mixture is stirred at 60° C. for 16 hours. Solvents are removed in vacuo and the residue is then dissolved in water. The solution is acidified to pH 1 with 10% aqueous hydrochloric acid solution and then extracted thrice with ethyl acetate. The combined extracts are washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, decanted, and concentrated under reduced pressure to afford a light orange oil, which solidified to a straw colored crystalline solid (0.46 g, 100%). MS (ES−): (M−H)=207.0
Workup
- customSolvents are removed in vacuo
- dissolutionthe residue is then dissolved in water
- extractionextracted thrice with ethyl acetate
- washThe combined extracts are washed with saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customdecanted
- concentrationconcentrated under reduced pressure
- customto afford a light orange oil, which
Sources & evidence
- ORD record
- ord-ebc311adef5046d7bd70ce4eb4127a69
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07626023B2
Reaction notes
Loading…