Cyclobutanone → 2-Cyclobutylnaphthalene

HRID 1973965Notes

Reaction equation

HRID 1973965 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>>[CH: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.[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

4

Reactant 2

HCID 14496CyclobutanoneHCID 178418423HCID 178418423, compound

Product 2

HCID 203350012-CyclobutylnaphthaleneHCID 20335179Cyclobutanol, 1-(2-naphthalenyl)-

Procedure

2-Cyclobutylnaphthalene is prepared from 2-naphthylmagnesium bromide by treating the latter with cyclobutanone to furnish 2-(1'-hydroxycyclobutyl)-naphthalene, which is hydrogenolyzed with hydrogen in the presence of Raney nickel to furnish 2-cyclobutylnaphthalene.

Sources & evidence

ORD record
ord-9fdb102caa4f43688362c2e2ebea225c
Source dataset
uspto-grants-1976_12
Patent number
US03998966

Reaction notes

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