Reaction #50112

Reaction equation

epoxide

1,3,3-trichloro-2-vinyl-7-oxabicyclo[4.1.0]heptane

HCl

→

phenol

Yield 75.4%

3-chloro-2-vinylphenol

Yield 75.4%

Solvents

DMF

Conditions

Workup

1. 1
   Temperatureto reflux for 3 h 30 min
2. 2
   Extractionextracted with ether (4×20 cm3)
3. 3
   Dryingdried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated down
6. 6
   OtherThe crude product obtained
7. 7
   Otherwas purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95)

Procedure

0.84 g (3.69 mmol) of epoxide 2i in solution in 4 cm3 of anhydrous DMF were heated to reflux for 3 h 30 min. The solution was acidified (pH=1) with 3N HCl, extracted with ether (4×20 cm3), dried over MgSO4, filtered and evaporated down. The crude product obtained was purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95). 0.43 g of phenol 4f were obtained (macrobore GC purity>99%). The yield of compound 4f was 75.5%.

Source