Diethyl Ether → 2,2,6-Trichloro-6-fluoro-1,1-cyclohexane-diol

HRID 399328Notes

Reaction equation

HRID 399328 reaction equation
[Cl:1][C:2]1([Cl:11])[CH2:7][CH2:6][CH2:5][C:4]([Cl:9])([F:8])[CH:3]1[OH:10].C1C=C[NH+]=CC=1.[O-:18][Cr](Cl)(=O)=O.CCOCC>ClC(Cl)C>[Cl:1][C:2]1([Cl:11])[CH2:7][CH2:6][CH2:5][C:4]([Cl:9])([F:8])[C:3]1([OH:18])[OH:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 189709602,2,6-Trichloro-6-fluorocyclohexanolHCID 178418287HCID 178418287, compound

Product 1

HCID 189709462,2,6-Trichloro-6-fluoro-1,1-cyclohexane-diolYield 73.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

0.96 g (4.33 mmol) of trichlorofluoro alcohol 1b in solution in 10 cm3 of dichloroethane were introduced into a 25-cm3 round bottom flask fitted with a condenser and with magnetic stirring. 2.33 g (2.5 eq.) of PCC were added with a spatula and the mixture was heated to reflux under argon atmosphere for 7 h. The reaction mixture was allowed to cool and was then taken up with 100 cm3 of ether, the whole being filtered on florisil. The solvents were evaporated off, the residue was incorporated on silica and purified by flash chromatography (eluent: ether/petroleum ether=15/85 then 20/80). 0.03 g of starting alcohol 1b, that was approximately 3%, and 0.05 g of a mixture of alcohol 1b, diol 3a and 0.76 g of pure diol 3a were isolated. The yield of compound was therefore higher than 74%.

Workup

  1. customfitted with a condenser and with magnetic stirring
  2. temperaturethe mixture was heated
  3. temperatureto reflux under argon atmosphere for 7 h
  4. temperatureto cool
  5. filtrationthe whole being filtered on florisil
  6. customThe solvents were evaporated off
  7. custompurified by flash chromatography (eluent

Sources & evidence

ORD record
ord-6236406a9f734e2b906ddf82e99ec025
Source dataset
uspto-grants-1998_10
Patent number
US05817890

Reaction notes

Loading…