Acid-catalyzed hydrolysis of diphenyl malonate

Question

What are the complete, acid-catalyzed hydrolysis products (with application of heat) of diphenyl malonate?

According to me, they are phenol, carbon dioxide, and acetic acid.

The aqueous acid and heat conditions indicate to me that we are returning from the carboxylic acid derivative (ester) to the carboxylic acid. The mechanism involves protonation of the carbonyl oxygen and nucleophilic attack by water. This ejects alcohol (well, in this case, phenol).

The heat induces the malonic acid intermediate to decarboxylate and this results in the production of carbon dioxide and acetic acid.

Is my analysis correct?

Answer 1

If the question is "What are the products of hydrolysis of diphenyl malonate?", then my answer would be 2 equivalents of phenol and one equivalent of malonic acid.

If the question is "What are the products of diphenyl malonate when heated in an acid aqueous solution?", then my answer would be 2 equivalents of phenol, one equivalent of acetic acid, and one equivalent of carbon dioxide.

I see it sort of as a semantic question, since the hydrolysis of an ester gives an alcohol and a carboxylic acid, as you suggest. I don't consider decarboxylation to be a hydrolysis reaction, literally defined as cleavage of bonds by addition of water. Water isn't incorporated into the products of the decarboxylation step.