HCID 23114103, compound → HCID 23114251, compound
Reaction equation
O[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][C:4]=1[OH:11]>C(O)(=O)C.[C].[Pd]>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:2][C:3]2[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][C:4]=2[OH:11])=[CH:13][CH:14]=1)([CH3:20])[CH3:19]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 2-(hydroxy(4-isopropylphenyl)methyl)-3,5-dimethylphenol obtained in Reference Example 147 (12.3 g, 45.5 mmol) and 10%-palladium carbon (50% hydrous, 1.23 g) in acetic acid (90 mL) was heated under hydrogen atmosphere at 90° C. for 16 hours. The catalyst was removed, and the reaction solution was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, washed with 1 N aqueous sodium hydroxide solution and a saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain 10.5 g (yield 90%) of the title compound. Oily matter.
Workup
- customThe catalyst was removed
- concentrationthe reaction solution was concentrated under reduced pressure
- dissolutionThe obtained residue was dissolved in ethyl acetate
- washwashed with 1 N aqueous sodium hydroxide solution
- dry with materiala saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)
Sources & evidence
- ORD record
- ord-5eaad26ea99448589271fab56783c741
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465815B2
Reaction notes
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