4,4'-Dichlorobenzophenone → alpha,alpha-bis(4-Chlorophenyl)oxiranemethanol

HRID 845339Notes

Reaction equation

HRID 845339 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C([Mg]Br)=C.[CH2:21]1[CH2:25][O:24]CC1.[NH4+].[Cl-]>CCOCC>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)([CH:21]2[CH2:25][O:24]2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70344,4'-DichlorobenzophenoneHCID 25517Ammonium ChlorideHCID 178420667HCID 178420667, compound

Product 1

HCID 13534918alpha,alpha-bis(4-Chlorophenyl)oxiranemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6 g of 4,4'-dichlorobenzophenone in 200 mL of ether was added 30 mL of 1.4M vinylmagnesium bromide/THF at 0°. After being stirred at 25° for 20 minutes, the mixture was poured onto aqueous NH4Cl, partitioned, washed with brine, dried (MgSO4), filtered, and concentrated. The crude adduct was allowed to stand in 50 mL of methylene chloride with 5.8 g of m-chloroperbenzoic acid for 3 days at 25°. The mixture was diluted with CH2Cl2, washed with aqueous NaHSO3, aqueous NaHCO3, brine, dried (Na2SO4), concentrated, and chromatographed (150 mL SiO2 /30% CH2Cl2 in hexane) to provide 2.9 g of the title compound (after washing the concentrated fractions with pentane), m.p. 87°-88°.

Workup

  1. custompartitioned
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. waitto stand in 50 mL of methylene chloride with 5.8 g of m-chloroperbenzoic acid for 3 days at 25°
  7. additionThe mixture was diluted with CH2Cl2
  8. washwashed with aqueous NaHSO3, aqueous NaHCO3, brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customchromatographed (150 mL SiO2 /30% CH2Cl2 in hexane)

Sources & evidence

ORD record
ord-58760e6be0794cd2a898e62643450437
Source dataset
uspto-grants-1988_07
Patent number
US04758262

Reaction notes

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