The Reaction of Styrene Oxide with Methanol

Reeve, Wilkins; Christoffel, Ivan.

doi:10.1021/ja01160a014

Cited by 73 publications

(41 citation statements)

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“…This finding supports the two earlier reports by Chapman et al (3) and Winstein and Ingraham (15) claiming purely secondary ether formation on strong acid catalyzed ring opening of styrene oxide with methanol and does not correspond with Reeve and Christoffel's (16) finding that mixtures resulted. In the absence of benzoic acid 60% 2-ethoxy-2-phenylethanol 6a was formed.…”

Section: Resultssupporting

confidence: 89%

Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Hocking¹

1974

Can. J. Chem.

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Mixtures of ring-opened and other products of reactions of acetic or benzoic acids, or ethanol, or phenol with styrene oxide under various conditions can be qualitatively and quantitatively analyzed without isolation of the components by the use of n.m.r. This method, in the case of the ester products, avoids confusing the initial ring-opening result with the results observed after subsequent acyl migrations which readily occur in this type of system.

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Section: Resultssupporting

confidence: 89%

Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Hocking¹

1974

Can. J. Chem.

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“…General procedure for the preparation of alcohols 8-10 from styrene oxide followed a previously described method [16]. Yields and analytical data for the resultant products were as follows.…”

Section: Methodsmentioning

confidence: 99%

“…For substrates 9-11 the relevant benzyl alcohols 15-17 were prepared by alkoxide ring opening of styrene oxide [16].…”

Section: Synthesis Of Benzyl Ether Substrates 8-13mentioning

confidence: 99%

The role of organic fluorine in directing alkylation reactions via lithium chelation

Tenza

Northen

O’Hagan

et al. 2004

Journal of Fluorine Chemistry

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“…Carboxyl-tagged alpha-methoxyphenylacetic acid was prepared on a micro scale from benzaldehyde and sodium cyanide-C14 by a modification of the standard procedure (1,8) involving the successive preparation of mandelonitrile and mandelic acid and the conversion of the latter to MOPA by methylation with dimethyl sulfate.…”

Section: Methodsmentioning

confidence: 99%