Methanol → (R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

HRID 43256Notes

Reaction equation

HRID 43256 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

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2733641(-)-2-Chloromandelic acid

Product 1

HCID 11790232(R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetateYield 94%

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

  1. temperatureheated
  2. temperatureto reflux, till completion of reaction
  3. distillationThen excess of methanol was distilled off under reduced pressure
  4. washwashed with aqueous sodium bicarbonate solution
  5. 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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