Abstract
The diastereomeric repellents of p-menthane-3,8-diol were produced from citronellal by treatment with 0.25% sulfuric acid at 50 °C for 11 h to give 97.9% conversion and 92.3% selectivity and citronellal acetal by-products with only 2.7%. The crude products were crystallized from n-heptane at −50 °C for 20 h to give p-menthane-3,8-diols in 80% yield and high purity. The stereochemistry of the citronellal acetal by-products was determined by 2D NMR and NOE.
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