Trifluoroacetic acid → 1-(2,2-Dimethylpropyl)-4-[(prop-2-en-1-yl)oxy]benzene

Participants

Reaction Steps

1-(4-Allyloxyphenyl)-2,2-dimethylpropan-1-ol (1.2 g, 6.1 mmol) and trimethylsilane (mL, 61.0 mmol) were dissolved in dichloromethane (5.0 mL) and trifluoroacetic acid (2.1 g, 18.3 mmol) was added at 0° C. After 30 min, the reaction mixture was concentrated to give esentially pure 1-allyloxy-4-neopentylbenzene. The crude product was dissolved in 1,2,4-trichlorobenzene (5.0 mL) and the solution was heated to reflux for 4 hrs. Removal of solvent and chromatography of the residue on silica gel eluting with 9:1 hexane:ethyl acetate gave 0.70 g 2-allyl-4-(2,2-dimethyl-propyl)phenol.

Provenance & Evidence