Sulfuric Acid → Methyl 2-hydroxy-2-(naphthalen-2-yl)acetate

HRID 388251Notes

Reaction equation

HRID 388251 reaction equation
[OH:1][CH:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[C:21]([O-])(O)=O.[Na+]>CO>[OH:1][CH:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[C:3]([O:5][CH3:21])=[O:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 111381432-Naphthylglycolic acid

Product 1

HCID 53825712Methyl 2-hydroxy-2-(naphthalen-2-yl)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-hydroxy-2-(naphthalen-2-yl)acetic acid (0.75 g, 1 eq) in dry MeOH was added sulfuric acid (0.1 mL) dropwise and heated to reflux. Stirring was then continued for 2 hours. The reaction mixture was then cooled and poured into saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic fractions were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield an oil (0.63 g, 78%) that was not further purified.

Workup

  1. temperatureheated to reflux
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ecdc0f124ce34d328b0b7b8441117e44
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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