Hydroquinone → HCID 14618049, compound

Participants

Reaction Steps

100 g (1.0 mol) of hydroquinone were dissolved in 200 ml of methanol with heating and converted into the monosodium salt using 180 g of 30% strength by weight sodium methoxide solution. 132 g (1.0 mol) of the sodium salt were then added in portions at 5° C. to a mixture of 250 ml of dimethylformamide and 106 g (0.5 mol) of perfluorocyclopentene. After stirring at room temperature for 19 hours, the mixture was added to 500 ml of water, and the organic phase was separated off after addition of 1000 ml of methylene chloride and subsequently washed with 500 ml of water. After drying, the solvent was stripped off on a rotary evaporator. 177 g of a partly crystalline, oily material remained. For further purification, this was dissolved in 200 ml of ethanol and reprecipitated by addition of 100 ml of water. 143 g of a slightly oily product was obtained, which corresponds to 73% of theory. The spectroscopic data (mass spectrum and 19F nuclear magnetic resonance spectrum) corresponded to the product from Example 44a).

Provenance & Evidence