Nerol → Oxiranemethanol, 3-methyl-3-(4-methyl-3-pentenyl)-

Participants

Reaction Steps

Ohloff prepared the intermediate 3,7-dimethyl-octa-2,5-dien-1,7-diol from nerol by its photosensitized air oxidation followed by reduction and cyclisation with an acid to obtain racemic nerol oxide [G. Ohloff, K. H. Schulte-Elite & B. Willhalm Helv. Chim. Acta. 47, 602, 1964]. In another publication nerol was first subjected to epoxidation at C6–C7 double bond and the epoxy derivative so obtained was heated in dimethyl amine at 150° to give 3,7-dimethyl-6-dimethyl amino-2-octen-1,7-diol which on oxidation with hydrogen peroxide and pyrolysis at 180° C. gave a diol intermediate that on acid catalysed cyclisation led to the formation of nerol oxide [G. Ohloff & B. Lienhard Helv. Chim. Acta. 48, 182, 1965].

Provenance & Evidence