Hydrochloric Acid → (2R)-2-hydroxy-2-(2-methoxyphenyl)acetic acid

HRID 458744Notes

Reaction equation

HRID 458744 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@@H:9]([OH:14])[C:10]([O:12]C)=[O:11].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@@H:9]([OH:14])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 45114263167820-07-7

Product 1

HCID 53887132(2R)-2-hydroxy-2-(2-methoxyphenyl)acetic acidYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 19 g of methyl (2R)-2-(methoxyphenyl)-2-hydroxyethanoate (cf. Journal of Chemical Society, Parkintrans 1, 2253–2255 (1992)) in 50 ml of methanol, 50 ml of 3N aqueous sodium hydroxide solution was added, followed by 12 hours' stirring at room temperature. Distilling the methanol off under reduced pressure, the reaction liquid was acidified with 1N hydrochloric acid and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure, to provide 11 g of the title compound.

Workup

  1. distillationDistilling the methanol off under reduced pressure
  2. customthe reaction liquid
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a5ffd641a7f64176b44e30e1a178e266
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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