Carbonic acid, bis(1,1-dimethylethyl) ester → HCID 19359302, compound

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Reaction Conditions

Reaction Steps

38 g (0.28 mol) 3,4-dihydroxstyrene are dissolved in 1 l of tetrahydrofuran and the solution is cooled to 5° C. With stirring and cooling, 63 g (0.56 mol) of potassium tert-butylate are added over 20 min in increments such that the temperature of the mixture remains between 5° C. The mixture is stirred for 1 h at room temperature. Then a solution of 135.3 g (0.62 mol) of di-tert-butylcarbonate in a small amount of THF is added dropwise. After stirring for c. 3 h at room temperature, analysis by thin-layer chromatography (hexane/ethyl acetate 4:1) indicates the end of the reaction. The reaction mixture is poured on to 2 kg of ice and extracted twice with diethyl ether. The organic phase is washed twice with 1N NaOH and then with water, and dried. The solvent is then removed by distillation on a rotary evaporator. The viscous residue is purified by column chromatography (silica gel, hexane/ethyl acetate 4:1).

Provenance & Evidence