Reaction #54573

Reaction equation

ether

Sodium hydride

2,2-dimethyl-4-(3-trifluoromethylphenyl)chroman-7-ol

Chloroacetonitrile

→

title compound

7-Cyanomethyloxy-2,2-dimethyl-4-(3-trifluoromethylphenyl)chroman

Solvents

dimethylformamide

—

petrol

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.ADDITIONthe resulting oil was poured into water
3. 3
   ExtractionThe aqueous solution was extracted with ether
4. 4
   Dryingthe etheeal extracts were dried (MgSO4)
5. 5
   Otherevaporated under reduced pressure
6. 6
   Otherto yield an oil

Procedure

Sodium hydride (0.93 g, 80% dispersion in oil) was added to a solution of 2,2-dimethyl-4-(3-trifluoromethylphenyl)chroman-7-ol (containing 1 mole of carbon tetrachloride of crystallisation) (7.5 g) in dimethylformamide (25 ml). Chloroacetonitrile (1.76 g) was added and the mixture heated at 60° C. for 3 hours. The solvent was removed under reduced pressure and the resulting oil was poured into water. The aqueous solution was extracted with ether and the etheeal extracts were dried (MgSO4) and evaporated under reduced pressure to yield an oil. Chromatography on alumina with ether--petrol (40°-60° C.); 1:3 as eluate gave the title compound which crystallised on standing.

Source