Ester to acid chloride transformation

[jolly_math]

Homework Statement

Which best accomplishes the following transformation?

Relevant Equations

ester to acid chloride

Here are 2 options:
A)

B)

For both syntheses, a protecting group is added to the alcohol, the ester is hydrolyzed to a carboxylic acid, then it is turned into an acid chloride using SOCl2. The difference is that A is base-catalyzed and B is acid-catalyzed.

The correct answer is A, but I don't understand why B doesn't work or is worse than A.

Thank you.

 

[Borek]

Eons passed since I worked with these things, but quick googling for stability of silyl ethers seems to be suggesting it is pH dependent.

 

[jolly_math]

Eons passed since I worked with these things, but quick googling for stability of silyl ethers seems to be suggesting it is pH dependent.

I've never seen this in my textbook or the resources I've used so far though. Is this a commonly-known fact?

 

[Borek]

Even wiki states: "Reaction with acids (...) removes the silyl group when protection is no longer needed.", so my bet is yes, it is something quite well known.

 

[Mayhem]

This protection group is acid sensitive. Step 2 in B negates step 1.