Methanol → Methyl (2,3-dihydro-1H-inden-2-yl)acetate
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.[CH3:18]O>>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[CH2:10][C:11]([O:13][CH3:18])=[O:12]Participants
Procedure
Under nitrogen atmosphere, 2-(2,3-dihydro-1H-inden-2-yl)acetic acid (Lanc, 19.6 g, 111 mmol) was dissolved in methanol (100 mL) and cooled in an ice bath. Thionyl chloride (9.7 mL, 133 mmol) was slowly added dropwise thereto under stirring. After completing the dropwise addition, the ice bath was removed and the reaction solution was additionally stirred for 30 minutes. Upon the completion of the reaction, the reaction solution was added in small portions to ice-cold sodium bicarbonate solution under stirring. The reaction mixture was extracted twice with ethyl acetate, and the obtained organic layer was washed once with water, dried over anhydrous magnesium sulfate, and the reaction solution was concentrated to obtain the target compound (21.2 g, Yield 100%).
Workup
- temperaturecooled in an ice bath
- additionthe dropwise addition
- customthe ice bath was removed
- stirringthe reaction solution was additionally stirred for 30 minutes
- customUpon the completion of the reaction
- additionthe reaction solution was added in small portions to ice-cold sodium bicarbonate solution
- stirringunder stirring
- extractionThe reaction mixture was extracted twice with ethyl acetate
- washthe obtained organic layer was washed once with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationthe reaction solution was concentrated
Sources & evidence
- ORD record
- ord-daf2d37ea15548399e5777cf0650d3a4
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039514B2
Reaction notes
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