Used for protection of carbonyl groups as their acetals (1,3-dioxane) derivatives, in the presence of a catalyst, e.g. TsOH: J. Chem. Soc. (C), 244 (1962), pyridine hydrochloride: Bull. Soc. Chim. Fr., 2287 (1972), or Amberlyst? 15: J. Chem. Soc. Perkin 1, 158 (1979). Comparative studies have indicated that formation of acetals from this diol is slower than for ethylene glycol, as is acid catalyzed hydrolysis of the resulting 1,3-dioxanes of aldehydes in comparison with the 1,3-dioxolanes, whereas for ketones the reverse applies: J. Am. Chem. Soc., 80, 6350 (1958); 90, 1249, 1253 (1968). For a review of the preparation of acetals, see: Synthesis, 501 (1981). Conditions have been described for the protection of acrolein using anhydrous HBr in dichloromethane: Org. Synth. Coll., 7, 59 (1990). For use in the preparation of the cyclic acetal of cyclopropenone, see: Org. Synth. Coll., 8, 173 (1993).
