Acetone → HCID 13046229, compound

Participants

Reaction Steps

A solution of 12.3 g (E)-1,1-diethoxy-4-m-methoxyphenoxy)-2-methyl-2-butene is dissolved in 125 ml acetone and treated with 25 ml water and 2.5 g p-toluenesulfonic acid monohydrate and stirred under nitrogen for 2 hours. The solution is concentrated at room temperature and the two-phase residue extracted with 100 ml benzene. The benzene extract is washed with 25 ml of 10% aqueous potassium carbonate followed by 25 ml water, dried with sodium sulfate and concentrated to yield 0.5 g orange oil which is chromatographed on a Waters LC/500 HPLC using a 500 gm silica column using 10% diethylether-hexane. Recrystallization of the product fraction from hexane containing a small portion of diethylether yields 0.23 g of the desired product. m.p. 45°-8° C. Elemental Analysis. Calculated for C12H14O3 : C,69.88; H,6.84. Found: C,69.51; H,6.59.

Provenance & Evidence