Hydrochloric Acid → Cyclobutanol, 1-(2-naphthalenyl)-

HRID 1576449Notes

Reaction equation

HRID 1576449 reaction equation
[C:1]1([Mg]Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]1(=[O:17])[CH2:16][CH2:15][CH2:14]1.Cl>C(OCC)C>[OH:17][C:13]1([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14496CyclobutanoneHCID 178418298HCID 178418298, compound

Product 1

HCID 20335179Cyclobutanol, 1-(2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 23.1 g. of naphthyl magnesium bromide and 250 ml. of diethyl ether, 7 g. of cyclobutanone are slowly added. After the addition, the mixture is refluxed for one hour, cooled, acidified with aqueous hydrochloric acid and filtered. The product is isolated by methylene chloride extraction to furnish 2-(1'-hydroxycyclobutyl)-naphthalene. The product is hydrogenated in 200 ml. of ethanol with a molar equivalent of hydrogen in the presence of 50 g. of Raney nickel; the reaction mixture is filtered after the hydrogenation and evaporated to furnish 2-cyclobutylnaphthalene.

Workup

  1. additionTo a mixture of 23.1 g
  2. additionAfter the addition
  3. temperaturethe mixture is refluxed for one hour
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe product is isolated by methylene chloride extraction

Sources & evidence

ORD record
ord-bb76d4e13b6249af936a492a8f2cfae2
Source dataset
uspto-grants-1976_09
Patent number
US03980699

Reaction notes

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