Water → 3,3-bis(4-fluorophenyl)tetrahydro-2H-pyran-2-one

HRID 35308Notes

Reaction equation

HRID 35308 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:6]#N.S(=O)(=O)(O)[OH:23].[OH2:27]>C(O)(=O)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:4][CH2:3][CH2:2][O:27][C:6]2=[O:23])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 19883501alpha-(3-Chloropropyl)-4-fluoro-alpha-(4-fluorophenyl)benzeneacetonitrile

Product 1

HCID 142302603,3-bis(4-fluorophenyl)tetrahydro-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3 parts of α-(3-chloropropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetonitrile, 92 parts of concentrated sulfuric acid, 50 parts of water and 50 parts of acetic acid was stirred and refluxed for 24 hours. The reaction mixture was concentrated to about 100 parts and the product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was suspended in petroleumether. The product was filtered off and crystallized from 2,2'-oxybispropane, yielding 1.41 parts of 3,3-bis(4-fluorophenyl)tetrahydro-2H-pyran-2-one; mp. 122.4° C. (intermediate 15).

Workup

  1. temperaturerefluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated to about 100 parts
  3. extractionthe product was extracted with methylbenzene
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe product was filtered off
  9. customcrystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-ea054479cca846fdbbe06a2498cabeed
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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