Réaction #670237

Équation de réaction

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol

o-chloronitrobenzene

potassium hydroxide

hydrochloric acid

→

o-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtalenyl)-2-nitrophenol

Rendement 67.0%

Solvants

DMSO

dichloromethane

water

Conditions de réaction

Traitement

1. 1
   Lavagethe organic layer was washed with diluted hydrochloric acid and brine
2. 2
   AutreAfter dryness, the solvent was evaporated under reduced pressure
3. 3
   Autreto give a crude product (139.7 mg)
4. 4
   AutreThis crude product was purified by silica gel column chromatography (AcOEt:n-hexane=1:30)

Mode opératoire

DMSO (5 ml) was added to 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol (97 mg, 0.475 mmol), o-chloronitrobenzene (77 mg, 0.48 mmol) and potassium hydroxide (27 mg, 0.48 mmol), and the mixture was stirred at 90° C. for 17 hours and 30 minutes. To the reaction mixture, water, dichloromethane, and concentrated hydrochloric acid (1 ml) were added, and the organic layer was washed with diluted hydrochloric acid and brine. After dryness, the solvent was evaporated under reduced pressure to give a crude product (139.7 mg). This crude product was purified by silica gel column chromatography (AcOEt:n-hexane=1:30) to give o-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtalenyl)-2-nitrophenol (Compound 27, 103.1 mg, 67%, colorless oil)

Source