Reaction #63574

Reaction equation

water

2-chloroethanol

sulfuric acid

4-fluoro-α-(4-fluorophenyl)benzenemethanol

→

1,1'-[(2-chloroethoxy)methylene]bis[4-fluorobenzene]

Solvents

benzene

benzene

Conditions

Workup

1. 1
   Temperaturewas heated on a water-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Temperaturerefluxed for 4 hours
4. 4
   TemperatureAfter cooling the reaction mixture
5. 5
   OtherThe benzene layer was separated
6. 6
   Dryingdried over calcium chloride
7. 7
   Otherevaporated
8. 8
   workup.DISTILLATIONThe residue was distilled in vacuo

Procedure

A mixture of 20 parts of 2-chloroethanol, 3 parts of sulfuric acid and 16 parts of benzene was heated on a water-bath. Then there were added dropwise 35 parts of 4-fluoro-α-(4-fluorophenyl)benzenemethanol dissolved in 32 parts of benzene. After the addition was complete, the whole was stirred and refluxed for 4 hours. After cooling the reaction mixture was poured into water. The benzene layer was separated, dried over calcium chloride and evaporated. The residue was distilled in vacuo, yielding 35 parts of 1,1'-[(2-chloroethoxy)methylene]bis[4-fluorobenzene]; bp. 164°-166° C. at 1.5 mm. pressure; nD20 : 1.5462; d2020 : 1.2290 (intermediate 1).

Source