Reaction #3049

Reaction equation

Water

Allyl bromide

2-t-butylphenol

potassium carbonate

→

2-(1,1-dimethylethyl)phenoxypropene

Solvents

acetone

Conditions

Workup

1. 1
   Temperatureat reflux temperature for 50 hours
2. 2
   Otherthe resulting layers were separated
3. 3
   ExtractionThe aqueous layer was extracted with 600 ml of diethyl ether
4. 4
   Extractionextract
5. 5
   Dryingthe resulting solution was dried over sodium sulfate overnight
6. 6
   OtherAfter sodium sulfate removal
7. 7
   Otherthe solvent was evaporated
8. 8
   Otherto provide

Procedure

Allyl bromide (69.2 ml), 2-t-butylphenol (122.9 ml) and potassium carbonate (121.6 g) were stirred in 265 ml of acetone at reflux temperature for 50 hours and then cooled to 35° C. Water (600 ml) was added and the resulting layers were separated. The aqueous layer was extracted with 600 ml of diethyl ether. The organic layer was combined with the aqueous layer's ether extract and the resulting solution was dried over sodium sulfate overnight. After sodium sulfate removal, the solvent was evaporated to provide, after further workup, 147 g of the subtitled intermediate.

Source