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Synthesis 2006(15): 2543-2550  
DOI: 10.1055/s-2006-942480
PAPER
© Georg Thieme Verlag Stuttgart · New York

The HF/BF3-Catalysed Reaction of Substituted Benzenes with Carbon Monoxide­

J. Alexander Willemse*a, Barend C. B. Bezuidenhoudta, Cedric W. Holzapfelb
a Sasol Technology R&D, PO Box 1, Sasolburg, 1947, South Africa
Fax: +27(11)5224998; e-Mail: alex.willemse@sasol.com; Fax: +27(11)5223274; e-Mail: ben.bezuidenhoudt@sasol.com;
b Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
e-Mail: cwh@rau.ac.za;
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Publikationsverlauf

Received 10 February 2006
Publikationsdatum:
11. Juli 2006 (online)

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Abstract

The HF/BF3-catalysed reactions of phenol and anisole as well as substituted benzenes with CO were investigated as possible routes to commercially important aldehydes.

The results confirmed that HF and BF3 are required in (at least) stoi­chiometric amounts for effective formylation with CO. With the aim of effecting truly catalytic reaction conditions, the formylation reactions were carried out in ionic liquids. It was shown that phenol is a good substrate for formylation in certain ionic liquids.

Key words

aldehydes - phenols - electrophilic aromatic substitutions - ionic liquids - Lewis acids

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11

Although care should be taken in the handling of the highly reactive alcohol 16, it could be prepared in almost quantitative yield via NaBH3 reduction of the corresponding ketone.

14

Sasol Technology R&D, 2001, unpublished results.