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

HRID 633474Notes

Reaction equation

HRID 633474 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-hydroxyacetate

Procedure

In a 1 L flask, 120 g (0.643 mole) of (R)-2-chloromandelic acid, 480 ml methanol and 4.8 g concentrated sulfuric acid were added. The solution is then heated to reflux for 2 hours and excess methanol is distilled under vacuum. The oily residue was taken in 650 ml chloroform and washed with 240 gm aqueous solution of 10% potassium carbonate and concentrated under vacuum. 124.4 gm of methyl-(R)-2-hydroxy-2-(2-chlorophenyl)acetate was obtained in the form of a colorless oil.

Workup

  1. temperatureThe solution is then heated
  2. temperatureto reflux for 2 hours
  3. distillationexcess methanol is distilled under vacuum
  4. washwashed with 240 gm aqueous solution of 10% potassium carbonate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fc49ee8bafcc4639b4cdbb06ffeb2a71
Source dataset
uspto-grants-2016_04
Patent number
US09321785B2

Reaction notes

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