O[CH2:2]/[C:3](=[CH:5]\[CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])/[CH3:4].CC(CC=O)CCCC(O)(C)C.CC(=CCC/C(=C/CO)/C)C.OC/C=C(/C)\CCC=C(C)C.CC1(C)C2CC1CCC2=C.CC(C)=CCCC(C=C)=C.Cl>>[CH3:2][C:3](=[CH:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])[CH3:4]A primary use for hydroxycitronellol is as an intermediate in the synthesis of hydroxycitronellal, (7-hydroxy-3,7-dimethyloctan-1-al), a widely used perfumery material. Conventionally, in this synthesis, a mixture of geraniol and nerol is prepared from beta-pinene via myrcene hydrochloride and is partially hydrogenated to produce citronellol. Citronellol is then hydrated under acid conditions to produce hydroxycitronellol. It has also been made from myrcene by preparing the dihydrochloride and then chlorodihydrogeranyl acetate, followed by saponification and hydrogenation.1
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