Hydrochloric Acid → HCID 86706690, compound

Participants

Reaction Steps

6′-Bromo-5′-methylspiro[cyclohexane-1,2′-indene]-1′,4(3′H)-dione (Intermediate 2, 1.38 g, 4.49 mmol) and propan-2-ol (16.6 mL, 215 mmol) were heated to 75° C. Ground NaOH (0.176 g, 4.40 mmol) was added. The resulting mixture was heated at reflux for 1.5 h and was then allowed to cool to r.t. The mixture was concentrated to half the volume and then water (15 mL) and toluene (15 mL) were added together with 6 M aq. HCl (0.749 mL, 4.49 mmol). The layers were separated and the aqueous layer was re-extracted with toluene (15 mL). The combined organic layers were dried over Na2SO4, concentrated and dried in vacuo to afford 1.36 g (98% yield) of the title compound as a mixture of isomers (˜70:30 mixture of isomers with the hydroxyl group in equatorial and axial position) and this mixture was used in the next step without further purification: MS (ES+) m/z 308, 311 [M+H]+.

Provenance & Evidence