Abstract
Racemic and enantiomerically enriched oxy-derivatives of gem-dimethylcyclohexene as potential components of fragrance and flavoring compositions were synthesized. Ethyl esters (2a–d), alcohols (3a–d), acetates (4a–d), propionates (5a–d) and aldehydes (6a–d) were obtained from racemic and enantiomerically enriched gem-dimethylcyclohexenols (1a–d). In the first step allyl alcohols (1a–d) were transformed via the Claisen rearrangement into respective ethyl esters (2a–d), which were subjected to reduction (LiAlH4) affording the corresponding alcohols (3a–d). The acetates (4a–c) and propionates (5a–c) were synthesized in the standard manner in the reaction of alcohols 3a–d with the respective acetyl or propionyl chlorides. Alcohols (3a–d) were also oxidized with chromium(vi) oxide, a pyridine complex giving aldehydes (6a–d), respectively. All esters, alcohols 3c and 3d, and aldehydes 6b and 6c possess valuable odoriferous properties, which could be useful for the cosmetic and food industries. Copyright © 2011 John Wiley & Sons, Ltd.
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