Ethanol → Ethyl 2-(4-bromophenyl)acetate

HRID 1869061Notes

Reaction equation

HRID 1869061 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 7020609Ethyl 2-(4-bromophenyl)acetate

Procedure

A solution of 63 grams (0.29 mole) of 4-bromophenyl acetic acid and 50 milliliters of concentrated sulfuric acid in 500 milliliters of absolute ethanol was refluxed for 8 hours then allowed to stand overnight. After pouring over 600 grams of ice, the mixture was extracted with ether/hexanes. The ether extracts were washed thoroughly with water and sodium bicarbonate solution then dried over anhydrous sodium sulfate. Removal of the solvent by rotary evaporation yielded 57 grams (0.24 mole, 80% isolated yield) of an oil which crystallized upon cooling. Filtration and washing with hexane afforded pure product.

Workup

  1. extractionthe mixture was extracted with ether/hexanes
  2. washThe ether extracts were washed thoroughly with water and sodium bicarbonate solution
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. customRemoval of the solvent
  5. customby rotary evaporation
  6. customyielded
  7. custom57 grams (0.24 mole, 80% isolated yield) of an oil which
  8. customcrystallized
  9. temperatureupon cooling
  10. filtrationFiltration
  11. washwashing with hexane afforded pure product

Sources & evidence

ORD record
ord-d1da105aefee4176bf23163131c9e169
Source dataset
uspto-grants-2009_12
Patent number
US07635741B2

Reaction notes

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