Allyl-t-butylmethylsilyl groups were shown to function as alcohol protecting groups whose hydrolytic stability was greater than t-butyldimethylsilyl (TBS) and Si(SiMe 3 ) 3 (sisyl) groups. Pseudo-first-order rate constants for the acidic hydrolysis of primary, benzylic, and secondary allyl-t-butylmethylsilyl ethers in AcOD/THF-d 8 /D 2 O were determined to be 2.94x10 - 3 , 8.26x10 - 4 , and 8.26x10 - 4 s - 1 , respectively. The regioselectivity of acidic hydrolysis of allylbenzyloxy-t-butylmethylsilane 1 was examined under strong acid (p-TsOH/CD 2 Cl 2 ) and weak acid (AcOD/THF-d 8 /D 2 O) conditions. In both cases, benzyl alcohol was initially produced exclusively from silicon-oxygen bond cleavage: allylic cleavage was only subsequently observed over time. However, the allyl group of the silyl ether could be hydrosilylated. The resulting alkoxy-functionalized disiloxane had greater hydrolytic stability under acidic conditions than the starting alkoxyallyl-t-butylmethylsilane.