Hydrochloric Acid → 2-(2-Naphthyl)toluene

HRID 356835

Reaction equation

HRID 356835 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.Cl>C1(C)C=CC=CC=1.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:3]1[CH:2]=[CH:11][CH:10]=[CH:9][C:4]=1[CH3:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 113722-Bromonaphthalene

Product 1

HCID 210519422-(2-Naphthyl)tolueneYield 172%

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 1140TolueneSolvent

Procedure

The Grignard solution was subsequently added dropwise to a solution of 120 g (0.57 mol) of 2-bromonaphthalene and 3.5 g of bis(triphenylphosphine)nickel dichloride in 800 cm3 of toluene at such a rate that the internal temperature did not exceed 50° C. The mixture was subsequently refluxed for a further 3 hours, 500 ml of 10% strength aqueous HCl were added, the phases were separated, and the organic phase was freed from solvents in vacuo. Filtration through silica gel (hexane) gave 107 g (87%) of 25 as a colorless oil.

Workup

  1. customdid not exceed 50° C
  2. temperatureThe mixture was subsequently refluxed for a further 3 hours
  3. customthe phases were separated
  4. filtrationFiltration through silica gel (hexane)

Sources & evidence

ORD record
ord-4120622199644d6789680e4f9027aec5
Source dataset
uspto-grants-1998_11
Patent number
US05840644

Linked notes

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