Trichloromethyl carbinols are known to afford α-substituted carboxylic acid derivatives upon treatment with base and an appropriate nucleophile (Jocic-type reaction). The mechanism involves an intermediate gem-dichloroepoxide that undergoes regioselective substitution with an added nucleophile. We have devised an inexpensive two-step oxidative one-carbon homologation of aldehydes to carboxylic acids in a Jocic-type reaction.  The approach is of broad scope, and offers high yields with all substrates examined.  Additionally, we have developed a new protecting group for aromatic aldehydes involving trichloromethyl methyl silyl ethers.  The protecting group is installed under mild conditions to afford masked aryl aldehydes in excellent yields.  This robust functionality is stable to acid and base hydrolysis, orthogonal to acetal protecting groups, and conveniently removed to reveal the aldehyde during global desilylation procedures.  We will disclose these results and related studies, thereby highlighting the versatility of trichloromethyl carbinols in general synthetic applications.