Ethanol → Ethyl 2-(4-fluorophenoxy)acetate

HRID 262884Notes

Reaction equation

HRID 262884 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH2:18]([O:9][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=1)[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 678824-Fluorophenoxyacetic acid

Product 1

HCID 4476170Ethyl 2-(4-fluorophenoxy)acetate

Procedure

To a stirred solution of 50 g (0.29 moles) of p-fluorophenoxy acetic acid in one liter of absolute ethanol is added 10 ml of sulfuric acid. The mixture is heated to reflux for 18 hours, cooled to room temperature, and evaporated under vacuum. It is then poured onto 300 g of ice, extracted twice with 500 ml of ether, washed twice with 250 ml of a saturated solution of sodium bicarbonate, 100ml of saturated sodium chloride solution, dried with magnesium sulfate, filtered and evaporated under vacuum giving 58 g of an oil. This is crystallized from 50 ml of hexane at -25° C. to give 55 g (90%) of the subject product as colorless crystals, mp 32°-33° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 18 hours
  3. customevaporated under vacuum
  4. additionIt is then poured onto 300 g of ice
  5. extractionextracted twice with 500 ml of ether
  6. washwashed twice with 250 ml of a saturated solution of sodium bicarbonate, 100ml of saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-3a1310ee9d614570aa0e02086f7d97a0
Source dataset
uspto-grants-1979_05
Patent number
US04154954

Reaction notes

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