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

HRID 537386Notes

Reaction equation

HRID 537386 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].P(=O)(Cl)(Cl)Cl.[CH3:18]O>>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C@@H:4]([OH:8])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24813Phosphorus oxychlorideHCID 2733641(-)-2-Chloromandelic acid

Product 1

HCID 11790232(R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetateYield 95%

Procedure

15 g of (R)-2-chloromandelic acid was mixed with methanol (CH3OH, 150 ml) and phosphorus chloride oxide (POCl3, 0.76 ml) in a flask by stirring using a magnetic stirrer at the room temperature for 6 hours. When the reaction was completed, the obtained product was washed with an aqueous solution of sodium sulfite (Na2SO3) and ethylacetate (EA). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4), filtrated, and concentrated under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (15.64 g, yield 95%).

Workup

  1. customat the room temperature
  2. customfor 6 hours
  3. washthe obtained product was washed with an aqueous solution of sodium sulfite (Na2SO3) and ethylacetate (EA)
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrated residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-25129f185ee64f75bede769f0a90c2d3
Source dataset
uspto-grants-2014_10
Patent number
US08859817B2

Reaction notes

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