Acetic Acid → HCID 20227997, compound

HRID 1731586Notes

Reaction equation

HRID 1731586 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[K+].C(O)(=O)C.[I-].[Na+].ClC(C)[C:14]([C:16]1[CH:21]=[C:20]([F:22])[C:19]([O:23][CH3:24])=[C:18]([F:25])[CH:17]=1)=[O:15]>CC(C)=O.O>[F:22][C:20]1[CH:21]=[C:16]([CH:14]([OH:15])[CH:1]([OH:4])[CH3:2])[CH:17]=[C:18]([F:25])[C:19]=1[O:23][CH3:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 517044Potassium AcetateHCID 20227994HCID 20227994, compound

Product 1

HCID 20227997HCID 20227997, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Potassium acetate (3.0 g) then glacial acetic acid (5 ml) and then sodium iodide (1.0 g) were added to a solution of 2-chloro-1-(3,5-difluoro-4-methoxyphenyl) propan-1-one (6.5 g) in acetone (50 ml). The mixture was stirred and heated under reflux for 4 hours, cooled and treated with water (150 ml) the acetone was evaporated and the aqueous residue was extracted into dichloromethane. The organic phase was washed with sodium bicarbonate solution, dried (magnesium sulphate), and concentrated under reduced pressure, the residual oil was dissolved in ethanol (150 ml) cooled in ice and treated with excess sodium borohydride (1.5 g). The solution was stirred for 2 hours at ambient temperature, the ethanol and the residue partitioned between dilute hydrochloric acid and ethyl acetate. The ethyl acetate layer was dried (magnesium sulphate) and evaporated to give 1-(3,5-difluoro-4-methoxy-phenyl)propane 1,2-diol as an oil which was used in the next stage without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customwas evaporated
  5. extractionthe aqueous residue was extracted into dichloromethane
  6. washThe organic phase was washed with sodium bicarbonate solution
  7. dry with materialdried (magnesium sulphate)
  8. concentrationconcentrated under reduced pressure
  9. dissolutionthe residual oil was dissolved in ethanol (150 ml)
  10. temperaturecooled in ice
  11. additiontreated with excess sodium borohydride (1.5 g)
  12. stirringThe solution was stirred for 2 hours at ambient temperature
  13. customthe ethanol and the residue partitioned between dilute hydrochloric acid and ethyl acetate
  14. dry with materialThe ethyl acetate layer was dried (magnesium sulphate)
  15. customevaporated

Sources & evidence

ORD record
ord-0a20ef7d9a9c407b8e6783e97ca1cf61
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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