Formaldehyde → 5-(Hydroxymethyl)uracil

Participants

Reaction Steps

To a 40 mL aqueous solution containing 0.60 gram of KOH were added 1.2 g of uracil and 5 mL of a 36.5% aqueous solution of formaldehyde. The resulting mixture was stirred in an oil bath set at 50° C. and the reaction was allowed to proceed until the complete disappearance of the starting uracil as observed by thin layer chromatography (TLC). The total reaction time was 72 hours under a nitrogen atmosphere. The reaction mixture was diluted with 80 mL of distilled water and vigorously stirred as 2.0 g of Amberlite resin IRC-50 (H) was added. The mixture was stirred for an extra 30-minute period and the pH was verified to ensure that the mixture was slightly acidic before proceeding. The resin was removed by filtration, and the filtrate was concentrated by vacuum distillation to a volume of approximately 25 mL. The solution was allowed to cool to room temperature, then further cooled in an ice bath to precipitate the product as a white solid. Recrystallization of the product was performed from water-methanol (volume ratio 1:2) and the product was filtered out, washed with cold methanol and dried under high vacuum to yield 827 mg of a fine white powder (54.4% yield) showing a single on TLC, with the Rf value 0.69 (methanol solvent) and properties given below.

Provenance & Evidence