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

HRID 1284337Notes

Reaction equation

HRID 1284337 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 hydrocloric 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-9d86124ad24f4201af6e1833d9c63751
Source dataset
uspto-grants-1976_08
Patent number
US03978116

Reaction notes

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