Hydrochloric Acid → 2-(2-Naphthyl)toluene

HRID 1106962Notes

Reaction equation

HRID 1106962 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 chloride in 800 cm3 of toluene at such a rate that the internal temperature did not exceed 50° C. Subsequently, the mixture was heated under reflux for a further 3 hours, admixed with 500 ml of 10% strength aqueous HCl, the phases were separated and the organic phase was freed of solvent under reduced pressure. Filtration through silica gel (hexane) gave 107 g (87%) of 13 as a colorless oil.

Workup

  1. customdid not exceed 50° C
  2. temperatureSubsequently, the mixture was heated
  3. temperatureunder reflux for a further 3 hours
  4. customthe phases were separated
  5. filtrationFiltration through silica gel (hexane)

Sources & evidence

ORD record
ord-8ac7844c41cc4556bbefbb36a36983fd
Source dataset
uspto-grants-2000_05
Patent number
US06057408

Reaction notes

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