Hydrochloric Acid → 2-Methyl-5-phenylbenzyl methanesulfonate
Reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4][OH:5].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].Cl>C(OCC)(=O)C>[CH3:23][S:24]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:9][C:2]=1[CH3:1])(=[O:26])=[O:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
2.00 g (10.1 mmol) of 2-methyl-5-phenylbenzyl alcohol was dissolved in 100 ml of ethyl acetate, and to this solution was added 4.2 ml (30.3 mmol) of triethylamine and the mixture was cooled to 0° C. To the reaction mixture was slowly dropped 1.73 g (15.1 mmol) of methanesulfonyl chloride, and the reaction mixture was controlled to room temperature. After stirring for 1 hours at room temperature, the reaction mixture was made acidic by addition of 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and saturated saline sequentially, dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=4/1 (v/v)), to obtain 2.79 g of 2-methyl-5-phenylbenzyl methanesulfonate.
Workup
- customwas controlled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with a saturated sodium bicarbonate solution and saturated saline sequentially
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c2f071d447bc4431bddd9d92677252e0
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06762197B2
Reaction notes
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