Hydrochloric Acid → 2-Methoxy-6-(4-propylcyclohexenyl)naphthalene

HRID 992178Notes

Reaction equation

HRID 992178 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][CH3:14])[CH:7]=[CH:6]2.[CH2:15]([CH:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)[CH2:16][CH3:17].Cl>O1CCCC1>[CH3:14][O:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:21]3[CH2:22][CH2:23][CH:18]([CH2:15][CH2:16][CH3:17])[CH2:19][CH:20]=3)[CH:4]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787862-Bromo-6-methoxynaphthaleneHCID 1424824-PropylcyclohexanoneHCID 5462224Magnesium

Product 1

HCID 218693902-Methoxy-6-(4-propylcyclohexenyl)naphthaleneYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

5.7 g of magnesium was suspended in 12 ml of tetrahydrofuran. To the suspension was then added dropwise a solution of 50 g of 6-bromo-2-methoxynaphthalene in 200 ml of tetrahydrofuran at a rate such that tetrahydrofuran was gently refluxed. The reaction mixture was then further stirred for 1 hour. To the reaction solution was then added dropwise a solution of 30 g of 4-propylcyclohexanone in 120 ml of tetrahydrofuran at room temperature. The reaction mixture was then further stirred for 1 hour. To the reaction solution was then added 200 ml of a 10% hydrochloric acid. The reaction mixture was extracted with 300 ml of toluene, washed with water, saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. To the residue were then added 230 ml of toluene and 4.0 g of p-toluenesulfonic acid monohydrate. The reaction mixture was then heated under reflux for 3 hour. The reaction solution was allowed to cool to root temperature, washed with water, saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue was then recrystallized from ethanol to obtain 44.8 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene.

Workup

  1. temperaturewas gently refluxed
  2. stirringThe reaction mixture was then further stirred for 1 hour
  3. extractionThe reaction mixture was extracted with 300 ml of toluene
  4. washwashed with water, saturated aqueous solution of sodium bicarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off
  7. additionTo the residue were then added 230 ml of toluene and 4.0 g of p-toluenesulfonic acid monohydrate
  8. temperatureThe reaction mixture was then heated
  9. temperatureunder reflux for 3 hour
  10. temperatureto cool
  11. washwashed with water, saturated aqueous solution of sodium bicarbonate and saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThe solvent was then distilled off
  14. customThe residue was then recrystallized from ethanol

Sources & evidence

ORD record
ord-e64e35ec332e46429ebc2ef3460e22c9
Source dataset
uspto-grants-2002_10
Patent number
US06468607B1

Reaction notes

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