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

HRID 573468Notes

Reaction equation

HRID 573468 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 stiffing 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 concented 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. customThe concentrated residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-db7a9fccaa0d4dbcb335633847805a28
Source dataset
uspto-grants-2015_05
Patent number
US09029589B2

Reaction notes

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