2-Methoxy-6-(4-propylcyclohexenyl)naphthalene → HCID 178447821, compound

Temperature

120 °C

44.9 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene was dissolved in 800 ml of ethyl acetate. To the solution was then added 10 g of 5% palladium carbon. The reaction mixture was then stirred at a hydrogen pressure of 4 kg/cm2 for 6 hours. The catalyst was then removed by filtration. The solvent was then distilled off. The residue was then dissolved in 180 ml of N,N-dimethylformamide. To the solution was then added 18 g of potassium t-butoxide. The reaction mixture was then heated to a temperature of 120° C. with stirring for 1 hour. The reaction solution was then allowed to cool to room temperature. To the reaction solution was then added 70 ml of a 10% hydrochloric acid to cause crystallization. The crystal thus precipitated wax filtered off, washed with water, and then dried under reduced pressure. The crystal was then recrystallized from ethanol to obtain 28.0 g of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene.

1. customThe catalyst was then removed by filtration
2. distillationThe solvent was then distilled off
3. dissolutionThe residue was then dissolved in 180 ml of N,N-dimethylformamide
4. additionTo the solution was then added 18 g of potassium t-butoxide
5. temperatureto cool to room temperature
6. additionTo the reaction solution was then added 70 ml of a 10% hydrochloric acid
7. customcrystallization
8. filtrationThe crystal thus precipitated wax filtered off
9. washwashed with water
10. customdried under reduced pressure
11. customThe crystal was then recrystallized from ethanol

ORD record

ord-8d419faecabc4a078c91ec549419e15d

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06468607B1