Hydroxybenzylcyclopentadienes and derivatives thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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568731, C07C 3917

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active

044840101

ABSTRACT:
Hindered hydroxybenzylcyclopentadienes and derivatives thereof, useful as antioxidants, are prepared by reacting cyclopentadiene, an alkali metal, and a hindered p-methylphenol having a displaceable group attached to the methyl group in the presence of a non-protic solvent; or in one step, by reacting cyclopentadiene, hindered phenol that is devoid of a group in the para position, formaldehyde, an amine, water, and an alkali metal hydroxide in the presence of a phase transfer catalyst; or in one step, by reacting cyclopentadiene and a hindered substituted p-methyl-phenol containing a displaceable group, in the presence of a non-protic solvent, water, an alkali metal hydroxide and a phase transfer catalyst. These compounds readily dimerize whereas the bis compounds are prepared in presence of an excess amount of the substituted p-methylphenol.

REFERENCES:
patent: 2485966 (1949-10-01), Good et al.
patent: 2852568 (1958-09-01), Schmerling
patent: 2864868 (1958-12-01), Bader
patent: 3118953 (1964-01-01), Cutukovic
patent: 3379775 (1968-04-01), Sheridan et al.
patent: 3683033 (1972-08-01), Stockmann et al.
patent: 3689573 (1972-09-01), Klein et al.

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