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31.7.5.1.2.2 Variation 2: Via Alkyl Chlorosulfonates

DOI: 10.1055/sos-SD-031-00501

Chen, J.; Chiu, C. K.-F.Science of Synthesis, (200731681.

Phenols and alcohols react with alkyl chlorosulfonates[‌45‌] to furnish alkyl aryl sulfate diesters and dialkyl sulfate diesters, respectively, in high yield. Unlike aryl or alkyl hydrogen sulfates, sulfate diesters are usually stable enough to tolerate a variety of chemical transformations. Being uncharged also renders them easy to purify by silica gel chromatography. It is a practical strategy to use a sulfate diester as a surrogate for an aryl or alkyl hydrogen sulfate; one alkyl group serves as a temporary protecting group and can be removed under mild conditions later to regenerate the hydrogen sulfate, as shown in Scheme 27.

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References


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