5-methoxy-1-oxo-3,4-dihydro-2H-naphthalene-2-carbaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the product obtained in step (i) (23.8 g, 0.11 mol) and hydroxylamine hydrochloride (8.2 g, 0.12 mol) in methanol (300 ml) is refluxed for ten minutes and then evaporated off under vacuum. Water is added thereto and the mixture is extracted with ethyl ether affording 19 g of the compound indicated in the title; m.p. 84°-86° C. is refluxed for ten minutes evaporated off under vacuum Water is added the mixture is extracted with ethyl ether affording 19 g of the compound

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the product obtained in step (i) (23.8 g, 0.11 mol) and hydroxylamine hydrochloride (8.2 g, 0.12 mol) in methanol (300 ml) is refluxed for ten minutes and then evaporated off under vacuum. Water is added thereto and the mixture is extracted with ethyl ether affording 19 g of the compound indicated in the title; m.p. 84°-86° C. is refluxed for ten minutes evaporated off under vacuum Water is added the mixture is extracted with ethyl ether affording 19 g of the compound

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl formate (20 ml, 0.37 mol) in anhydrous benzene (100 ml) is added to sodium ethoxide, prepared from sodium (8.34 g, 0.35 mol) and absolute ethanol, in anhydrous benzene (100 ml). The reaction mixture is cooled to about 0° C. and a solution of 5-methoxy-3,4-dihydronaphthalen-1(2H)-one (25 g, 0.14 mol) in anhydrous benzene (100 ml) is then slowly stirred in. By working up the mixture as described in J. Am. Chem. Soc., 1947, 69, 2942, the above indicated product is recovered (24.8 g); m.p. 68°-70° C. , 1947, 69, 2942, the above indicated product is recovered (24.8 g)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-methoxy-1-tetralone (10 g) in diethyl ether (100 ml) at 0° C. was added 1M potassium t-butoxide in tetrahydrofuran (68 ml) with stirring. After 15 minutes, ethyl formate (25 g) was added in one portion, and the reaction mixture allowed to rise to room temperature over a period of 45 minutes. The mixture was poured into water (500 ml), extracted with diethyl ether, the ether extract dried over magnesium sulfate, and solvent removed under reduced pressure to give 2-formyl-5-methoxy-1-tetralone (10.2 g), m.p. 67°-68° C. to rise to room temperature over a period of 45 minutes extracted with diethyl ether the ether extract dried over magnesium sulfate, and solvent removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the product obtained in step (i) (23.8 g, 0.11 mol) and hydroxylamine hydrochloride (8.2 g, 0.12 mol) in methanol (300 ml) is refluxed for ten minutes and then evaporated off under vacuum. Water is added thereto and the mixture is extracted with ethyl ether affording 19 g of the compound indicated in the title; m.p. 84°-86° C. is refluxed for ten minutes evaporated off under vacuum Water is added the mixture is extracted with ethyl ether affording 19 g of the compound

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl formate (20 ml, 0.37 mol) in anhydrous benzene (100 ml) is added to sodium ethoxide, prepared from sodium (8.34 g, 0.35 mol) and absolute ethanol, in anhydrous benzene (100 ml). The reaction mixture is cooled to about 0° C. and a solution of 5-methoxy-3,4-dihydronaphthalen-1(2H)-one (25 g, 0.14 mol) in anhydrous benzene (100 ml) is then slowly stirred in. By working up the mixture as described in J. Am. Chem. Soc., 1947, 69, 2942, the above indicated product is recovered (24.8 g); m.p. 68°-70° C. , 1947, 69, 2942, the above indicated product is recovered (24.8 g)