Solid State Acetylation with Acetylimidazole: Selective Protection of Primary Alcohols and Phenols

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• A typical experimental procedure is as follows: A mixture of alcohol 1 and acetylimidazole 2 (1.5∼2 equiv.) was ground well with a pestle in a mortar at room temperature in ambient atmosphere. After manual grinding occasionally at a certain period of time, a mixture of solid began to be wet and melted finally. The reaction was monitored by tlc using a capillary tube keeping ethyl acetate or ethanol inside (usually the reaction completed in 2 hr). The reaction was worked up by dilution with ethyl acetate, and the resulting solution was passed through an SiO2 short column. Evaporation of the solvent left residue which was purified by flash column or medium pressure liquid chromatography to afford the acetate 3
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