Reaction #50113

Reaction equation

epoxide

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

HCl

→

phenol

Yield 88.8%

2-allyl -3-chlorophenol

Yield 88.8%

Solvents

DMF

Conditions

Workup

1. 1
   Temperatureto reflux for 5 h
2. 2
   Extractionextracted with ether
3. 3
   Concentrationconcentrated
4. 4
   workup.ADDITIONa 3N sodium hydroxide solution was added to the ether phase (while the mixture
5. 5
   Otherwas removed
6. 6
   Washthe material washed once with ether
7. 7
   Extractionextracted with ether (4×30 cm3)
8. 8
   Dryingdried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Otherevaporated down

Procedure

2 g (8.28 mmol) of epoxide 2j in solution in 5 cm3 of anhydrous DMF were heated to reflux for 5 h. The solution was acidified (pH<1) with 3N HCl, extracted with ether and concentrated, and a 3N sodium hydroxide solution was added to the ether phase (while the mixture was kept stirred for 5 to 10 min), the ether phase was removed and the material washed once with ether. The aqueous phase was acidified using a solution with 3N HCl (pH=1) and extracted with ether (4×30 cm3), dried over MgSO4, filtered and evaporated down. 1.24 g of phenol 4g were obtained as a liquid whose macrobore GC purity was higher than The yield of phenol 4g was 89%.

Source