1-Propanol → n-Propyl 2-(2-fluoro-4-hydroxyphenoxy)propionate

HRID 542094Notes

Reaction equation

HRID 542094 reaction equation
[CH2:1](O)[CH2:2][CH3:3].[F:5][C:6]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:7]=1[O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11]>S(=O)(=O)(O)O.ClC(Cl)C>[F:5][C:6]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:7]=1[O:8][CH:9]([CH3:13])[C:10]([O:12][CH2:1][CH2:2][CH3:3])=[O:11]

Participants

5

Reactant 2

HCID 10311-PropanolHCID 198631662-(2-Fluoro-4-hydroxyphenoxy)propionic acid

Product 1

HCID 13578010n-Propyl 2-(2-fluoro-4-hydroxyphenoxy)propionateYield 35.5%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

(ii) n-Propanol (35 ml) and concentrated sulfuric acid (6 drops) were added to a solution of crude 2-(2-fluoro-4-hydroxyphenoxy)propionic acid (8.6 g) in dichloroethane (13 ml). The mixture was heated under reflux with stirring for a period of 6.5 hours, cooled, and the solvent was evaporated under reduced pressure. The residue was treated with water and the aqueous mixture was extracted with dichloromethane. The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and then with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to give an oil (5.7 g; 54.8%). The oil was purified by vacuum distillation to give n-propyl 2-(2-fluoro-4-hydroxyphenoxy)propionate (3.7 g; 35.5%); bp 210°-220° C. at 0.1 mm Hg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was treated with water
  6. extractionthe aqueous mixture was extracted with dichloromethane
  7. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate
  8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customto give an oil (5.7 g; 54.8%)
  12. distillationThe oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-d96d4e7e7b074ccdb567de5d1c8000f0
Source dataset
uspto-grants-1987_04
Patent number
US04655819

Reaction notes

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