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

HRID 857589Notes

Reaction equation

HRID 857589 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH:14]=3)[CH:9]=2)[CH:4]=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C@H:13]3[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)[CH:9]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 218693902-Methoxy-6-(4-propylcyclohexenyl)naphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 178447821HCID 178447821, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

44.8 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 causes crystallization. The crystal thus precipitated was 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.

Workup

  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. customto causes crystallization
  8. customThe crystal thus precipitated
  9. filtrationwas filtered off
  10. washwashed with water
  11. customdried under reduced pressure
  12. customThe crystal was then recrystallized from ethanol

Sources & evidence

ORD record
ord-0bda3192e7914f5d9f39567be739ab29
Source dataset
uspto-grants-2006_12
Patent number
US07145047B2

Reaction notes

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