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

HRID 2071849Notes

Reaction equation

HRID 2071849 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[Mg]Br.[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 178418423HCID 178418423, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 23.1 g. of 2-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 was isolated by methylene chloride extraction to furnish 2-(1'-hydroxycyclobutyl)-napthalene. 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 hydrogenolysis 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 was isolated by methylene chloride extraction

Sources & evidence

ORD record
ord-c892a3a3de7846e3b54faaa54ca26b6b
Source dataset
uspto-grants-1977_09
Patent number
US04048330

Reaction notes

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