Acetic Acid → 2-Hydroxydecanoic Acid

Participants

Reaction Steps

Either of the diastereomeric salts so formed may then be reacted with a mineral or organic acid (e.g., sulfuric or acetic acid) in an inert solvent such as ethylacetate, water, acetone or toluene, preferably ethyl acetate, to yield the pure enantiomer of 2-hydroxydecanoic acid having the same stereochemistry at the carbon alpha to the carbonyl group (e.g., VII→VIII in scheme 2). The reaction temperature may range from about -78° C. to about 100° C., but is preferably about room temperature. Either of the resulting pure enantiomers of 2-hydroxydecanoic acid can then be converted into the pure enantiomer of methyl-2-hydroxydecanoate having the same stereochemistry at the carbon alpha to the carbonyl group by treatment with methanol and hydrochloric acid at a temperature from about -78° C. to about 100° C. (e.g., VIII→IX in scheme 2). The solvent may be methanol or another inert, polar, aprotic solvent such as methanol/THF, methanol/methylene chloride or methanol/toluene.

Provenance & Evidence