Hydrochloric Acid → (Methylphenyl)naphthalene

HRID 356832

Reaction equation

HRID 356832 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][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>[C:2]1([C:5]2[CH:4]=[CH:3][CH:2]=[CH:11][C:6]=2[CH3:7])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70011-Bromonaphthalene

Product 1

HCID 3016790(Methylphenyl)naphthaleneYield 184.8%

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 1140TolueneSolvent

Procedure

The Grignard solution was subsequently added dropwise to a solution of 118 g (0.57 mol) of 1-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 solvent in vacuo. Filtration through silica gel (hexane) gave 115 g (92%) of 18 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-e0195a9011ef48d796ff404674952ade
Source dataset
uspto-grants-1998_11
Patent number
US05840644

Linked notes

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