Regioselective Substitution of Phenols with Trifluoroacetaldehyde Ethyl Hemiacetal

Phenol did not react directly with trifluoroacetaldehyde ethyl hemiacetal. In the presence of catalytic amounts of anhydrous potassium carbonate, however, the reaction readily occurred. The p-substituted product 4-(2,2,2-trifluoro-1-hydroxyethyl)phenol predominated. In contrast, the reaction catalyz...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 74; no. 2; pp. 377 - 383
Main Authors Gong, Yuefa, Kato, Katsuya, Kimoto, Hiroshi
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.02.2001
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
KETONES
ETHERS
REDUCTION
CARBONYL-COMPOUNDS
BAKERS-YEAST
GENERATION
ASYMMETRIC ELECTROPHILIC SUBSTITUTION
ALPHA-TRIFLUOROMETHYLATED ALCOHOLS
FRIEDEL-CRAFTS REACTION
DERIVATIVES
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Summary:Phenol did not react directly with trifluoroacetaldehyde ethyl hemiacetal. In the presence of catalytic amounts of anhydrous potassium carbonate, however, the reaction readily occurred. The p-substituted product 4-(2,2,2-trifluoro-1-hydroxyethyl)phenol predominated. In contrast, the reaction catalyzed by zinc halide predominantly produced the o-substituted product. Corresponding reactions of several phenols were studied under the same catalytic conditions.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.74.377