Water → 2,6-Dichloro-2,6-difluorocyclohexanol

HRID 21825Notes

Reaction equation

HRID 21825 reaction equation
B(F)(F)[F:2].CCOCC.[Cl:10][C:11]12O[CH:16]1[CH2:15][CH2:14][C:13]([Cl:19])([F:18])[CH2:12]2.[OH2:20]>ClCCCl>[Cl:10][C:11]1([F:2])[CH2:16][CH2:15][CH2:14][C:13]([Cl:19])([F:18])[CH:12]1[OH:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709542,6-Dichloro-2,6-difluorocyclohexanol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

0.47 cm3 (0.55 eq.) of BF3.Et2O were added to 1.89 g (7.03 mmol) of epoxide 2e in solution in 20 cm3 of 1,2-dichloroethane. The reaction mixture was heated to reflux under argon atmosphere for 1 h 45 min and then hydrolyzed hot with 30 cm3 of distilled water (stirring was continued for 10 min). It was extracted with dichloromethane (4×15 cm3) and then dried over MgSO4, filtered and evaporated down. 1.43 g of alcohol 1g were obtained, the macrobore GC purity of which was higher than 97%. The yield of alcohol 1g was 98%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under argon atmosphere for 1 h 45 min
  3. extractionIt was extracted with dichloromethane (4×15 cm3)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated down

Sources & evidence

ORD record
ord-b86355ea42cc4b5fafaa71ce19546561
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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