This is kind of highly speculative, but bear with me: the techniques and reactions used are well-studied.
The addition of hypochlorite to an alkene produces a chlorohydrin, a vicinal chloro-alcohol. The addition of hypochlorite to methacrylic acid produces a combination of two possible chlorohydrins, one with the chlorine on the tertiary hydrogen and one with the chlorine on the primary hydrogen. The dehydrohalogenation of these with a base produces an epoxide; this is the most common procedure for the preparation of epoxides.
Epoxides are capable of a Friedel-Crafts type reaction -- here's a review. In particular, propylene oxide leads to 1-aryl-2-propanols, and so will methacrylic acid lead to 3-aryl-2-methyl-lactic acids.
The 3-aryl-2-methyl lactic acid produced here is a tertiary alpha-hydroxy acid. Fuming sulfuric acid is able to decarboxylate tertiary alpha-hydroxy acids to produce ketones, here's the writeup:
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0010
A concern with the use of fuming sulfuric acid is that this reagent is known to attack aryl ethers; however, I believe that is only an issue at refluxing conditions. The decarboxylation is conducted cold, and it happens rather fast, which should prevent most ether-cleavage. Another concern is that this reaction produces carbon monoxide, which is extremely dangerous, odorless, and necessitates excellent ventilation (having a carbon monoxide detector around wouldn't hurt!).
The thing I don't know -- I became interested in this when I heard that methacrylic acid could be obtained by depolymerizing acrylic resins. I don't know the specifics, though, so I don't know how viable that is. I also don't know what catalyst is ideal for the arylation -- I'm guessing ZnCl2 just because I always guess ZnCl2, but H3PO4 or something else might work better.
The addition of hypochlorite to an alkene produces a chlorohydrin, a vicinal chloro-alcohol. The addition of hypochlorite to methacrylic acid produces a combination of two possible chlorohydrins, one with the chlorine on the tertiary hydrogen and one with the chlorine on the primary hydrogen. The dehydrohalogenation of these with a base produces an epoxide; this is the most common procedure for the preparation of epoxides.
Epoxides are capable of a Friedel-Crafts type reaction -- here's a review. In particular, propylene oxide leads to 1-aryl-2-propanols, and so will methacrylic acid lead to 3-aryl-2-methyl-lactic acids.
The 3-aryl-2-methyl lactic acid produced here is a tertiary alpha-hydroxy acid. Fuming sulfuric acid is able to decarboxylate tertiary alpha-hydroxy acids to produce ketones, here's the writeup:
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0010
A concern with the use of fuming sulfuric acid is that this reagent is known to attack aryl ethers; however, I believe that is only an issue at refluxing conditions. The decarboxylation is conducted cold, and it happens rather fast, which should prevent most ether-cleavage. Another concern is that this reaction produces carbon monoxide, which is extremely dangerous, odorless, and necessitates excellent ventilation (having a carbon monoxide detector around wouldn't hurt!).
The thing I don't know -- I became interested in this when I heard that methacrylic acid could be obtained by depolymerizing acrylic resins. I don't know the specifics, though, so I don't know how viable that is. I also don't know what catalyst is ideal for the arylation -- I'm guessing ZnCl2 just because I always guess ZnCl2, but H3PO4 or something else might work better.