Reaction #670237

Reaction equation

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

Yield 67.0%

Solvents

DMSO

dichloromethane

water

Conditions

Workup

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

Procedure

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