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2,2-Dimethoxypropane acts as a dehydrating agent. It also serves as an intermediate in the synthesis of vitamin E, vitamin A and various carotenoids such as astaxanthin. It is used as a reagent for the preparation of 1,2-diols, acetonides, isopropylidene derivatives of sugars, nucleosides, methyl esters of amino acids and enol ethers.
Methoxylating agent for preparation of acetals by acid-catalyzed exchange: J. Org. Chem., 25, 521 (1960). Also used as a water-scavenger in the preparation of acetals from higher-boiling alcohols and ketones: Org. Synth. Coll., 5, 292 (1973).
Widely used for the isopropylidenation of diols; see, e.g.: Org. Synth. Coll., 9, 450, 717 (1998). Isopropylidenation of acid-sensitive carbohydrates in the presence of 2,3-Dichloro-5,6-dicyanobenzoquinone, A11879: Acta Chem. Scand., 47, 843 (1993); preparation of acyclic mixed acetals of carbohydrates: Acta Chem. Scand., 48, 80 (1994). For use in the cyclization of N-Boc serine methyl ester to the oxazolidine, see: Org. Synth. Coll., 9, 300 (1998).
Methyl ester hydrochlorides of amino acids can be conveniently prepared with excess reagent in combination with conc. HCl. Water is removed in situ, thus displacing the equilibrium in favor of the ester: J. Org. Chem., 28, 3898 (1963). Methyl esters of non-aromatic acids can also be prepared with the reagent in MeOH with a catalytic amount of HCl or TMS chloride: Tetrahedron Lett., 38, 2685 (1997)./n
Urosa, A.; Marcos, I. S.; Díez, D.; Padrón, J. M.; Pilar Basabe, P. Synthesis of Luffarin L and 16-epi-Luffarin L Using a Temporary Silicon-Tethered Ring-Closing Metathesis Reaction. J. Org. Chem. 2015, 80 (12), 6447-6455.
Gefahrenhinweise (EU): H225-H319
Highly flammable liquid and vapour. Causes serious eye irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.