Patchoulol

[citation needed] Gal first isolated patchouli alcohol in 1869, and Montgolfier later formulated its chemical composition (correctly) as C15H26O.

[4] After several years of careful degradation study, Büchi and co-workers proposed that patchouli alcohol had the structure 1.

A subsequent synthesis of material which corresponded to an authentic sample of natural patchouli alcohol appeared to verify Büchi's proposal.

Dunitz et al. had undertaken X-ray analysis of the patchouli alcohol diester with chromic acid, intending to determine the Cr-O-C angles.

The discrepancy had resulted from an unanticipated skeletal rearrangement when patchoulene was treated with peroxy acid in Büchi's confirmatory synthesis.

Proposed sequence for the synthesis of patchouli alcohol.
Proposed sequence for the synthesis of patchouli alcohol.
Actual sequence for the synthesis of patchouli alcohol. Contains embedded bicyclo[2.2.2]octane motif.
Actual sequence for the synthesis of patchouli alcohol. Contains embedded bicyclo[2.2.2]octane motif.