Hydrochloric Acid → (1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

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Reaction Conditions

Reaction Steps

A solution of Example 49C (2.65 g, 8.02 mmol) in 1,4-dioxane (25 mL) was treated with aqueous 1 N hydrochloric acid solution (25 mL) and refluxed for 3 hours. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated in hot hexane and dried to give 1.62 g (61%) of the title compound. 1H NMR (300 MHz, CDCl3): δ ppm 0.43 m, 0.5 H) 0.83 m, 10 H) 1.06 (m, 0.5 H) 1.51 (s, 1.5 H) 1.56 (s, 1.5 H) 1.83 m, 1 H) 2.02 m, 0.5 H) 2.26 m, 0.5 H) 3.74 (s, 1 H) 6.09 (s, 0.5 H) 7.51 m, 3 H) 8.10 (td, J=7.81, 1.29 Hz, 1 H); MS (ESI−) m/z 257 (M−H)−.

Provenance & Evidence