Methyl iodide → 2,2-dimethyl-1-tetralone

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%).

1. additionwas added
2. temperatureThe mixture was heated on an oil bath to 40° C. for 30 minutes
3. stirringstirring
4. customcontinued at RT until the starting material
5. customThe reaction was quenched by addition of water (slowly and dropwise)
6. customto destroy excess sodium hydride
7. extractionThe mixture was extracted with ethyl acetate
8. washwashed with water
9. dry with materialdried over sodium sulphate
10. customEvaporation of the solvent
11. customyielded a brown oil

ORD record

ord-fbd601463ce64f5f93490a849c7e8b70

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969249B2