Cyclobutyl phenyl ketone → 2-Phenylbicyclo[1.1.1]pentan-2-ol

HRID 2280801Notes

Reaction equation

HRID 2280801 reaction equation
[CH:1]1([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1>C1C=CC=CC=1.[Hg]>[C:7]1([C:5]2([OH:6])[CH:3]3[CH2:2][CH:1]2[CH2:4]3)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 79414Cyclobutyl phenyl ketone

Product 1

HCID 1402712-Phenylbicyclo[1.1.1]pentan-2-olYield 30%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 241BenzeneSolvent

Procedure

A stirring solution of cyclobutyl(phenyl)methanone (3.0 g, 18.8 mmol) in 800 ml of benzene was irradiated with a 1000 W mercury arc lamp for 48 h at room temperature in a nitrogen atmosphere. The solution was concentrated and the residue (3.1 g) was purified by column chromatography (10%-25% ethyl acetate in petroleum ether) to give the desired product as a white solid (0.9 g, 5.6 mmol, yield: 30%). 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.28 (m, 5H), 3.04 (s, 2H), 2.82 (dd, J1=10.2 Hz, J2=2.4 Hz, 1H), 2.09 (s, 1H), 1.78 (d, J=2.4 Hz, 1H), 1.50 (d, J=3.3 Hz, 1H), 1.33 (dd, J1=9.9, J2=3.3 Hz, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue (3.1 g) was purified by column chromatography (10%-25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2f72b58473b241179a41e0d0734da1b6
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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