Acetone → (-)-(R)-3-(4-fluorophenoxy)-1,2-propanediol

HRID 1085683Notes

Reaction equation

HRID 1085683 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C@H:8]2[CH2:12][O:11]C(C)(C)[O:9]2)=[CH:4][CH:3]=1.Cl.CC(=O)C>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@H:8]([OH:9])[CH2:12][OH:11])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 15725175(S)-4-[(4-fluorophenoxy)methyl]-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 11321370(-)-(R)-3-(4-fluorophenoxy)-1,2-propanediolYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26 parts of (S)-4-[(4-fluorophenoxy)methyl]-2,2-dimethyl-1,3-dioxolane, 35 parts of a hydrochloric acid solution 2N and 80 parts of 2-propanone was stirred for 2 hours at reflux temperature. The mixture was stirred overnight at room temperature, diluted with 240 parts of ethanol and evaporated. The residue was dissolved in trichloromethane. The organic layer was washed twice with water, dried, filtered and evaporated. The residue was crystallized from tetrachloromethane. The product was filtered off and dried, yielding 11 parts (50.4%) of (-)-(R)-3-(4-fluorophenoxy)-1,2-propanediol; [α]D =-10.08° (c=0.5% in methanol) (146).

Workup

  1. temperatureat reflux temperature
  2. stirringThe mixture was stirred overnight at room temperature
  3. customevaporated
  4. dissolutionThe residue was dissolved in trichloromethane
  5. washThe organic layer was washed twice with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from tetrachloromethane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-4f69d974e81e4402a2746061bd209171
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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