1-Naphthalenol, 2-(4-morpholinylmethyl)- → 2-Methyl-1-naphthol

Participants

Reaction Steps

Research Disclosure, January 1975, 27, concerns incorporated dye-forming blocked developers. In accordance with the process disclosed, a mixture of 65.7 g (0.37 mole) of 2-morpholinomethyl-1-naphthol, 15 g of 10% Pd/C, and 540 ml of ethanol was hydrogenated at ambient temperature and at an initial pressure of 62 psi. The theoretical amount of hydrogen was absorbed in approximately one hour. The catalyst was removed by filtration and the filtrate was concentrated under vacuum. The residue was taken up in ether, extracted with 10% hydrochloric acid then with saturated aqueous NaCl, dried over anhydrous sodium sulfate, then concentrated under vacuum to yield 37.9 g 2-methyl-1-naphthol (65% yield). The acetate (1) was prepared in a yield of 61% using acetic anhydride-pyridine. The overall yield was 40%. This prior art process is disadvantageous in that the intermediate compound, 2-morpholinomethyl-1-naphthol, does not precipitate from water, thus an extraction step is required. Moreover, high loading (20%) of 10% Pd/C is required. Still further, both an extraction step and acetylation step are necessary. Thus, the entire process disadvantageously requires three steps.

Provenance & Evidence