Sulfuric Acid → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 1004071Notes

Reaction equation

HRID 1004071 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[CH3:18][O:10][C:9](=[O:11])[C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-(3-chloro-phenyl)-hydroxy-acetic acid (19.98 g) in methanol (250 ml) containing concentrated sulphuric acid (1 ml) was heated under reflux for 6.5 h. The solution was cooled, neutralised with aqueous sodium bicarbonate solution, and concentrated. The residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution, dried, and evaporated to give the title compound (21.13 g) as a pale-yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6.5 h
  3. temperatureThe solution was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with aqueous sodium bicarbonate solution
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-507cf87ec1fc4f8188216dbaa001f800
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

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