Water → HCID 24974018, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the relevant 2-hydroxy-spiro[5.5]undecan-2,7-diene-3-carboxylic acid methyl ester isomer (9) or (9′) (19.0 g, 85.0 mmol) in DMSO (66 mL) was added NaCl (5.5 g, 93.5 mmol) and H2O (4.6 mL, 255 mmol). The reaction mixture was heated at 160° C. for 6 hours then cooled and poured into H2O (100 mL). The aqueous layer was extracted with Et2O (5×) and the combined organic layers dried over anhydrous MgSO4. The solvent was removed in vacuo and the resulting residue purified over silica (n-pentane/Et2O, 95:5) to afford 13.3 g (95% yield) of the desired product as a colorless oil which was characterized as follows:

Provenance & Evidence