Hydrochloric Acid → 2-Methoxy-6-propylnaphthalene

HRID 992182Notes

Reaction equation

HRID 992182 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[CH2:14](Br)[CH2:15][CH3:16].[Mg].Cl>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl.O>[CH3:13][O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH2:14][CH2:15][CH3:16])[CH:3]=2)[CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78401-BromopropaneHCID 787862-Bromo-6-methoxynaphthaleneHCID 5462224Magnesium

Product 1

HCID 30236632-Methoxy-6-propylnaphthaleneYield 101.8%

Reagents, catalysts & solvents 3

HCID 2734542[1,2-Bis(diphenylphosphino)ethane]dichloronickel(II)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 g of 2-bromo-6-methoxynaphthalene and 2.5 g of dichloro[1,2-bis(diphenylphosphino)ethane]nickel (II) in 200 ml of tetrahydrofuran (THF) was added dropwise a Grignard reagent prepared from 125 g of propyl bromide and 27 g of magnesium under nitrogen atomsphere. The reaction mixture was further stirred for 1 hour, and then poured into water. To the reaction mixture was then added diluted hydrochloric acid. The resulting organic phase was then separated. The resulting aqueous phase was extracted with toluene. The organic phase and the material thus extracted were together washed sequentially with water, saturated aqueous solution of sodium bicarbonate, water and saturated brine, and then dehydrated and dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain 172 g of 2-methoxy-6-propylnaphthalene.

Workup

  1. customThe resulting organic phase was then separated
  2. extractionThe resulting aqueous phase was extracted with toluene
  3. extractionThe organic phase and the material thus extracted
  4. washwere together washed sequentially with water, saturated aqueous solution of sodium bicarbonate, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-98420df65afb4476ac6d8818898a423d
Source dataset
uspto-grants-2002_10
Patent number
US06468607B1

Reaction notes

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