Methanol → (R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate
Reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C@@H:4]([OH:8])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C@H:4]([OH:8])[C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1]Participants
4
Procedure
In a four necked round bottomed flask, 500 gm of (R)-2-chloromandelic acid was taken in 2600 ml methanol. Then 18.8 gm of sulfuric acid was added and heated to reflux, till completion of reaction. Then excess of methanol was distilled off under reduced pressure. Residue was taken in dichloromethane and washed with aqueous sodium bicarbonate solution. Dichloromethane was distilled under reduced pressure to obtain 522 gm of Methyl-(R)-2-hydroxy-2-(2-chlorophenyl)acetate as an oil. Yield: 94%. Purity: 98.5%
Workup
- temperatureheated
- temperatureto reflux, till completion of reaction
- distillationThen excess of methanol was distilled off under reduced pressure
- washwashed with aqueous sodium bicarbonate solution
- distillationDichloromethane was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-913661c25fe14ba9b913906057d5cd6a
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536337B2
Reaction notes
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