Reaction #50099

Reaction equation

sodium hydroxide

2,2,6,6-tetrachlorocyclohexanol

ethyl ether

→

epoxide

1,3,3-trichloro-7-oxabicyclo[4.1.0]heptane

Solvents

water

Conditions

Workup

1. 1
   workup.WAITwas continued for 5 min
2. 2
   Otherthe phases were separated
3. 3
   Extractionthe aqueous phase was extracted with ether (6×50 cm3)
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationthe mixture was concentrated with a rotary evaporator

Procedure

7 g (175 mmol) of sodium hydroxide pellets were added in three portions at 10°-15° C. to 15.2 g (63.88 mmol) of 2,2,6,6-tetrachlorocyclohexanol 1a in suspension in 70 cm3 of distilled water. The reaction mixture was kept at room temperature for 1 h 15 min, 20 cm3 of ethyl ether were then added, stirring was continued for 5 min and then the phases were separated and the aqueous phase was extracted with ether (6×50 cm3). The ether phases were combined, dried over MgSO4, filtered, and the mixture was concentrated with a rotary evaporator. A liquid epoxide 2a (m=12.42 g) was obtained, representing 96.5% of the theoretical yield. The compound 2a will be frequently employed without further purification in the following stages (semicapillary GC purity>96%). The epoxide 2a can be purified by distillation at reduced pressure (boiling at 40° C. at 0.1 mm Hg); after distillation, the yield of compound 2a was 92%.

Source