2,2-dimethyl-3,4-dihydronaphthalen-1-one

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

Procedure: To a suspension of NaH (8.2 gm, 343 mmol) in THF (250 mL) in a one-liter round bottomed flask, 1-tetralone [11] (10.0 gm, 69 mmol) dissolved in dry THF (25 mL) was added. After stirring the mixture for 10 minutes at RT, methyl iodide (11.1 ml, 178 mmol) was added via a syringe. The mixture was heated on an oil bath to 40° C. for 30 minutes, and stirring continued at RT until the starting material disappeared. The reaction was monitored by TLC using ethyl acetate:hexane (1:6) solvent mixture. The reaction was quenched by addition of water (slowly and dropwise) to destroy excess sodium hydride. The mixture was extracted with ethyl acetate, washed with water and dried over sodium sulphate. Evaporation of the solvent yielded a brown oil. Column chromatography using silica gel with EtOAc:Hexane (1:6) afforded clean 2,2-dimethyl-1-tetralone [12](10.8 g, 83%). was added The mixture was heated on an oil bath to 40° C. for 30 minutes stirring continued at RT until the starting material The reaction was quenched by addition of water (slowly and dropwise) to destroy excess sodium hydride The mixture was extracted with ethyl acetate washed with water dried over sodium sulphate Evaporation of the solvent yielded a brown oil

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

Procedure: 6-Fluoro-2,2-dimethyl-1-indanone, a white crystalline solid melting at 64.5°-66.5° C. and 2,2-dimethyl-1-tetralone, a colorless liquid boiling at 88°-89° C. under 0.75 mm Hg (100 Pascals) pressure were prepared similarly.

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

Procedure: To a suspension of NaH (8.2 gm, 343 mmol) in THF (250 mL) in a one-liter round bottomed flask, 1-tetralone [11] (10.0 gm, 69 mmol) dissolved in dry THF (25 mL) was added. After stirring the mixture for 10 minutes at RT, methyl iodide (11.1 ml, 178 mmol) was added via a syringe. The mixture was heated on an oil bath to 40° C. for 30 minutes, and stirring continued at RT until the starting material disappeared. The reaction was monitored by TLC using ethyl acetate:hexane (1:6) solvent mixture. The reaction was quenched by addition of water (slowly and dropwise) to destroy excess sodium hydride. The mixture was extracted with ethyl acetate, washed with water and dried over sodium sulphate. Evaporation of the solvent yielded a brown oil. Column chromatography using silica gel with EtOAc:Hexane (1:6) afforded clean 2,2-dimethyl-1-tetralone [12](10.8 g, 83%). was added The mixture was heated on an oil bath to 40° C. for 30 minutes stirring continued at RT until the starting material The reaction was quenched by addition of water (slowly and dropwise) to destroy excess sodium hydride The mixture was extracted with ethyl acetate washed with water dried over sodium sulphate Evaporation of the solvent yielded a brown oil