9 a) Ac02H; b, 0,; c, m-CPBA; d, MeONaIMeOH; e, (PyH)2Cr207; 9 iso-C3HSLi; g) NaI-Zn-NaOAc-HOAc; h, H+ or HO-. 0018-019X/79/7/2168-06$01.00/0 0 1979 Schweizerische Chemische Gesellschaft Hydrogenation of (+)-(R)and (-)-(S)-p-mentha-1,8dien-4-01~ (1) [ 191. -The dienol (R)-1 (or (S)-I) (0.1 g) was hydrogenated in ethanol (2 ml) over Raney nickel (50 mg). After quantitative absorption of 1 equiv. of HZ, the catalyst was filtered off and the solvent evaporated. The residue consisted of a single product (12), which was further purified by GC. (lo'?? SE-30, 3m, 150") to measure its specific rotation. 2) 3, Epoxy ketone 7. -IR.: 1710s cm-I. -IH-NMR.: 1.45 (s, 3 H); 2.25 (br. s, 4H); 2.76 (m, 2H) and 3.14 ppm (m, 1 H). The optical purity of the starting (+)-(R)-limonene being 82% ([a@= -k 103.3" (neat), compared with the published value of + 125.6" (neat) [25]), the corrected [a@ values of (R)-1 and (S)-1 are + 10.0" and -9.8" respectively.