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2,2-Dimethoxypropane

2,2-Dimethoxypropane (DMP) is an organic compound with the formula (CH3)2C(OCH3)2. A colorless liquid, it is the product of the condensation of acetone and methanol. DMP is used as a water scavenger in water-sensitive reactions. Upon acid-catalyzed reaction, DMP reacts quantitatively with water to form acetone and methanol. This property can be used to accurately determine the amount of water in a sample, alternatively to the Karl Fischer method.

DMP is used to prepare acetonides from diols, where it is both a synthon for acetone and a scavenger for the water byproduct: :

It can also be used to prepare methyl esters from carboxylic acids, where it acts as a water scavenger and source of methanol: : :

Dimethoxypropane is an intermediate for the synthesis of 2-methoxypropene.

In histology, DMP is used for the dehydration of animal tissue.

References

References

  1. [http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=D136808|SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 2,2-Dimethoxypropane] at [[Sigma-Aldrich]]
  2. (1961). "Water determination by reaction with 2, 2-dimethoxypropane". Anal. Chem..
  3. (1965). "Gas chromatographic method of moisture determination". J. Pharm. Sci..
  4. (1995). "D-(''R'')-Glyceraldehyde Acetonide". Org. Synth..
  5. (1995). "L-(''S'')-glyceraldehyde Acetonide". Org. Synth..
  6. (1959). "Notes- Use of Acetone Dimethyl Acetal in Preparation of Methyl Esters". The Journal of Organic Chemistry.
  7. (1978). "Rapid dehydration--clearing with 2,2-dimethoxypropane for paraffin embedding". J. Histochem. Cytochem..
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