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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 12
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Original Articles

Selective Alkylations of Certain Phenolic and Enolic Functions with Lithium Carbonate/Alkyl Halide

Walter E. Wymann Institute of Organic Chemistry, Syntex Research, Palo Alto, CA, 94304
,
Roman Davis Institute of Organic Chemistry, Syntex Research, Palo Alto, CA, 94304
,
John W. Patterson Jr. Institute of Organic Chemistry, Syntex Research, Palo Alto, CA, 94304
&
Jürg R. Pfister Institute of Organic Chemistry, Syntex Research, Palo Alto, CA, 94304
Pages 1379-1384 | Published online: 19 Dec 2006
 
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Abstract

Phenolic groups with pKa ≤ 8 (due to the presence of electron withdrawing groups in the orho- or para- position) can be alkylated selectively with Li2CO3/alkyl halide/DMF; less acidic phenolic groups are unreactive. Even though chelated phenolic/enolic functions have unexpectedly high experimental pKa′s (∼10), they can be alkylated with this reagent combination.

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