Hydrochloric Acid → HCID 58240634, compound

Participants

Reaction Steps

2,2,8,8-Tetramethyl-5-oxatetracyclo[7.2.1.01.7.04.6]dodec-6-yl acetate (3, 14.5 g, 61% pure, 0.032 mol) was added at r. t. to a solution of sodium hydroxide (30 g, 0.75 mol) in water (0.75 l) and ethanol (0.75 l). After overnight stirring at r. t., the reaction mixture was neutralized to pH 7 with 2M aqueous HCl solution and extracted with MTBE (2×0.5 l). The combined organic phases were washed with water (2×0.2 l), dried (Na2SO4) and concentrated in vacuo to give crude 5-hydroxy-2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undecan-4-one (4, 13 g, colourless oil, partly solidifying on standing) which was used without further purification in the next steps. Besides two isomeric hydroxyketones, the mixture contained tautomeric forms of the oxidised 4 (diketone).

Provenance & Evidence