Water → 9-(Methoxymethyl)-9H-fluorene-9-methanol

Beteiligte Stoffe

Reaktionsschritte

Under nitrogen atmosphere and water-free conditions, to a reactor were added in succession 80 ml of THF, 22.6 g of 9,9-bis(hydroxymethyl)fluorene and 57 g of methyl iodide. After the reaction mixture was admixed homogeneously by stirring, 4.6 g of 52% NaH in mineral oil was added batch-wise over 2 hours at room temperature. Upon completing the addition, the reaction mixture was stirred for further 2 hours. The unreacted methyl iodide was recovered by distillation. The remainder was diluted with 100 ml of water, and extracted twice using 100 ml of diethyl ether for each time. The combined diethyl ether extract was dried over anhydrous sodium sulfate. After drying, the ether solution was evaporated to dryness to give 22.8 g of crude. The crude was purified through column chromatography to give 14.9 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (yield 62%).

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