Ethyl 1-naphthylacetate

ETHYL 1 -NAPHTHYLACETATE ESTER HOMOLOGATION VIA YNOLATE ANIONS... 

The pot material in this distillation is rather viscous and tends to bump, so good stirring and extra care should be employed to avoid this problem. A low-boiling fraction (0.67-0.78 g, 95-133°C, 0.2 mm) is collected that is mostly a mixture of hydrocarbons and ethyl 1 -naphthylacetate (ca. 1% yield). More than 90% of the product distils at 134-138°C, 0.2 mm. For the final few drops of product the bath temperature must be raised by 15-20°C, resulting in a slight rise in product boiling... 

Rajarathnam E. Reddy and Conrad J. Kowalski 146 ETHYL 1 -NAPHTHYLACETATE ESTER HOMOLOGATION VIA YNOLATE ANIONS... 

After the quench is complete, the mixture is diluted with 2 L of ether and washed in a separatory funnel with 1.25 L of aqueous 10% hydrochloric acid. The aqueous layer is reextracted with a 2-L portion of ether. The combined ethereal layers are washed with 1.25 L of saturated brine solution and dried over anhydrous magnesium sulfate. After filtration and removal of solvent using a rotary evaporator there remains 26 g of crude product as a reddish-brown oil. Distillation of this material under reduced pressure through an unpacked, 2-Inch distillation apparatus affords 17.3 g (81%) of ethyl 1-naphthylacetate as a yellow liquid, (bp 134-138°C, 0.2 mm) (Notes 17,18). 

Ethyl 1-naphthylacetate 1-Naphthaleneacetic acid, ethyl ester (8,9) (2122-70-5) Lithium 2,2,6,6-tetramethylpiperidide Piperidine, 2,2,6,6-tetramethyl-, lithium salt (9) (38227-87-1)... 

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. 

Ethyl 1-naphthylacet.ate has been prepared by ethanolysis of 1-naphthylacetonitrile under acidic conditions5 and by the Arndt-Eistert reaction of l-(diazoacetyl)naphtha ene with ethanol and silver oxide.6... 

ETHYL 1-NAPHTHYLACETATE (1-Naphthaleneacetic acid, ethyl ester)... 

Amdt-Eistert reaction (2,102-103, ref. 29a). The procedure for preparation of ethyl 1 -naphthylacetate has been published.2... 

Ethylidene iodide-Diethylzinc, 141 Ethylidenetriphenylphosphorane, 141—142 Ethyliodomethylzinc, 257-258 Ethyl 1-naphthylacetate, 74 N-Ethyl-N-nitrosourea, 73... 

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