Methanol → HCID 19754690, compound
Reaction equation
O[C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18]C=O)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CO.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:10][C:4]1([CH3:11])[CH2:5][C:6]([CH3:8])([CH3:9])[CH2:7][C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[CH:3]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of N-[2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]formamide (4.00 g, 14.5 mmol) in toluene (40 mL) was added pyridinium p-toluenesulfonate (365 mg, 1.45 mmol), followed by stirring at 110° C. for 1 hour. Then, the reaction mixture was cooled down to 50° C., methanol (40 mL) and a 5N aqueous solution of sodium hydroxide (14.5 mL) were added thereto, and the reaction mixture was stirred at 80° C. for 14 hours. The reaction mixture was allowed to cool down to room temperature, the aqueous layer was removed. The organic layer was washed with water and a 5% aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 3.33 g of the title compound as a brown oil.
Workup
- temperatureThen, the reaction mixture was cooled down to 50° C.
- stirringthe reaction mixture was stirred at 80° C. for 14 hours
- temperatureto cool down to room temperature
- customthe aqueous layer was removed
- washThe organic layer was washed with water
- dry with materiala 5% aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1e82328911aa41bcb2d1b3692865f9d9
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910734B2
Reaction notes
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