L<Diazoacetyl naphthalene

This compound is a severe skin irritant, hence great care should be exercised to avoid any contact. For best yields in the rearrangement step this crystallization is recommended, since I he yield of ethyl 1-naphthylacetate is reduced by about 20% if the crude product is used in the rearrangement. A sample of crystallized l-(diazoacetyl)naphthalene, m.p. 52-53°, that had been stored in a screw-top bottle in a refrigerator for about 2 weeks afforded the same yield of ethyl 1-naphthylacetate as a freshly prepared sample. 

The checkers obtained 26.1-26.5 g. (83-84.5%) of 1-(diazoacetyljnaphthalene, m.p. 47-49.5°, when 1-naphthoyl chloride prepared from commercial 1-naphthoic acid was used (ef. Notes 1 and 2). Recrystallization from hexane gave 24.6 g. (78%) of l-(diazoacetyl)naphthalene, m.p. 49.5-52°, that was used in Part B. 

Ethyl 1-naphthylacetate has been prepared by ethanolysis of l-naphthylacetonitrile under acidic conditions and by the Arndt-Eistert reaction of l-(diazoacetyl)naphthalene with ethanol and silver oxide. ... 

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