Réaction #955978

Équation de réaction

ethyl acetate hexane

NaH

1-tetralone

EtOAc Hexane

methyl iodide

→

2,2-dimethyl-1-tetralone

Rendement 83.0%

2,2-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

Rendement 83.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThe mixture was heated on an oil bath to 40° C. for 30 minutes
3. 3
   workup.STIRRINGstirring
4. 4
   Autrecontinued at RT until the starting material
5. 5
   AutreThe reaction was quenched by addition of water (slowly and dropwise)
6. 6
   Autreto destroy excess sodium hydride
7. 7
   ExtractionThe mixture was extracted with ethyl acetate
8. 8
   Lavagewashed with water
9. 9
   Séchagedried over sodium sulphate
10. 10
    AutreEvaporation of the solvent
11. 11
    Autreyielded a brown oil

Mode opératoire

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%).

Source