Cross-metathesis reactions of 1-hepten-3-ol, 1-octen-4-ol, 1-octen-4-yl acetate and 1-tetradecen-4-ol with unsaturated methyl esters were investigated to optimize the synthesis of methyl hydroxyalkenoates, precursors of hydroxyalkanoic acids. Various commercially available catalysts, concentration ratios of reagents as well as microwave irradiation were explored. (R)-8-hydroxydodecanoic acid and (S)-8-hydroxystearic acid were successfully obtained in 3 steps from enantiomerically enriched alcohols.