Ethanol → Ethyl diphenylacetate

HRID 2408822Notes

Reaction equation

HRID 2408822 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.[CH2:22](O)[CH3:23]>>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([O:10][CH2:22][CH3:23])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 8333Diphenylacetic Acid

Product 1

HCID 226748Ethyl diphenylacetate

Procedure

2,2-Diphenylacetic acid (50 g) was dissolved in ethanol (350 mL). Concentrated sulfuric acid (3 mL) was added, and the mixture was refluxed overnight. After cooling to room temperature, the reaction mixture was concentrated and diluted with diethyl ether. The organic solvent solution was then extracted with water, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was then dried with magnesium sulfate, filtered, and concentrated to obtain the title compound. MS (DCI+) m/z 241 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. concentrationthe reaction mixture was concentrated
  3. additiondiluted with diethyl ether
  4. extractionThe organic solvent solution was then extracted with water, saturated aqueous sodium bicarbonate solution, and brine
  5. dry with materialThe organic layer was then dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-881ea307a8534f0b8e336d0b45441773
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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