Ethanol → Ethyl 2-(4-fluorophenoxy)acetate

HRID 1449263Notes

Reaction equation

HRID 1449263 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, 100 ml 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, 100 ml of saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-bb7417dd745a49f58bf8ae6a9d16b3c2
Source dataset
uspto-grants-1980_02
Patent number
US04189597

Reaction notes

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