Sulfuric Acid → Methyl alpha-phenylbenzeneacetate

HRID 388257Notes

Reaction equation

HRID 388257 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:22]([O-])(O)=O.[Na+]>CO>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([O:10][CH3:22])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8333Diphenylacetic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 77019Methyl alpha-phenylbenzeneacetateYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2,2-diphenylacetic acid (1 gram, 1 equiv) in dry MeOH (50 mL) was added sulfuric acid (0.4 mL) dropwise and heated to reflux. Stirring was then continued for 3 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 (1.0 g, 93%) 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-4fd80ac317c540d0a47855ff3d37e48b
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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