A Convenient Synthesis of (Acyloxy)alkyl α-Ethers of Phenols

Article abstract of DOI:10.1021/jo00174a024

(Acyloxy)alkyl α-ethers (1) of phenols, thiophenol, and catechols have been prepared in good yield by their alkylation with (acyloxy)alkyl α-chlorides or iodides in acetone in the presence of K2CO3.In addition, one example of an (acylthio)alkyl α-ether was prepared.Either partial or complete acylation rather than alkylation on oxygen took place if the α-iodide was not used except for reactions of 3-chloro-1(3H)-isobenzofuranone with phenol or catechol or the reaction of (benzoylthio)methyl chloride with β-estradiol.It is suggested that more alkylation takes place with iodide as a leaving group because of the tighter transition state that develops with the better nucleofuge.The alkylation reaction sequence has two advantages for the synthesis of 1: (1) the mildness of the reaction conditions and (2) the wide variety of acyl and alkyl groups that can be incorporated into the product through the (acyloxy)alkyl α-halides.