Epichlorohydrin → HCID 13792150, compound

HRID 1584883Notes

Reaction equation

HRID 1584883 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[F:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([C:13](=[O:15])[CH3:14])[CH:12]=1.[OH-].[K+]>C(O)C.O>[O:5]1[CH2:4][CH:3]1[CH2:1][O:16][C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:12][C:11]=1[C:13](=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 13792150HCID 13792150, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Epichlorohydrin (38 g) was added to a stirred solution of 5'-fluoro-2'-hydroxyacetophenone (20.9 g) in ethanol (20 ml). A solution of potassium hydroxide (9.5 g) in a mixture of ethanol (30 ml) and water (5 ml) was then added and stirring continued for one hour. The solvent was removed in vacuo and the residue poured into water then extracted with ethyl acetate. The combined extracts were washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue purified by chromatography on silica, eluting with a 9:1 mixture, then a 3:2 mixture, of petroleum ether (b.p. 40-60° C.) and ethyl acetate. Appropriate fractions were combined and the solvent removed in vacuo to give 2'-(2,3-epoxypropoxy)-5'-fluoroacetophenone (4.68 g) as an oil.

Workup

  1. additionwas then added
  2. customThe solvent was removed in vacuo
  3. additionthe residue poured into water
  4. extractionthen extracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by chromatography on silica
  9. washeluting with a 9:1 mixture
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e4513043761547c28b1e7b28f7c4c33c
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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