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

HRID 1414647Notes

Reaction equation

HRID 1414647 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 1 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 1 hour
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe product is isolated by methylene chloride extraction

Sources & evidence

ORD record
ord-6ec3106654a14a78b67b0fccd86b0d72
Source dataset
uspto-grants-1977_01
Patent number
US04001301

Reaction notes

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