[asd34]

For paperwork I had to synthesize MON-0585 /2,6-ditert-butyl-4-(2-phenylpropan-2-yl)phenol/. I sent the attached file to the teacher, but he said it is not good, because "isomers!". I don't know what he mean, can someone help?

[discodermolide]

Friedel-Crafts reactions will always give positional isomers. The minute the first alkyl group goes on the possibility of isomer generation increases.
Have you been taught about transition metal coupling reactions yet?

[asd34]

Friedel-Crafts reactions will always give positional isomers. The minute the first alkyl group goes on the possibility of isomer generation increases.
Have you been taught about transition metal coupling reactions yet?

I found in wikipedia C-C bond formations with metals, in laboratory some of my friends do Ullmann reactions, it is possible to do with copper?

[discodermolide]

I was thinking more of Suzuki type reactions using SP_³-SP² coupling.

[asd34]

I draw two way, in the second is the sp3-sp3

[discodermolide]

Those may stand a better chance in your synthesis scheme.

[orgopete]

I am not advocating you do this for a textbook problem, so just think of this as an indication of chemical reactivity. It appears as though MON-0585 is prepared from 2,6-di-tert-butylphenol and 2-phenylpropan-2-ol with a mixture of acetic and formic acid. The di-tert-butylphenol is listed in Wikipedia and I found the patent listed in this reference, http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=161829.

It is sometimes surprising how similar textbook chemistry can be to commercial reactions. More esoteric routes may be superior, but not as economic.

[curiouscat]

It is sometimes surprising how similar textbook chemistry can be to commercial reactions. More esoteric routes may be superior, but not as economic.

Superior in what sense, if not economic, I was curious.

[orgopete]

It is sometimes surprising how similar textbook chemistry can be to commercial reactions. More esoteric routes may be superior, but not as economic.

Superior in what sense, if not economic, I was curious.

This is deference and ignorance. Disco suggested a Suzuki coupling. It could be a better reaction and involve more regioselectivity. I really don't know. I don't know the productivity of the patent route either.

None the less, in the patent route, the product is obtained directly from the electrophilic attack. If you are to produce a lot of this material, the patent route does look inviting to me. If you think about the patent route vs proposed synthesis, both depend upon a selective reaction of phenol. This is where the basic ortho-para direction of a phenol must be followed. It is difficult to overcome those basic chemical principles that textbooks describe.

[curiouscat]

It is sometimes surprising how similar textbook chemistry can be to commercial reactions. More esoteric routes may be superior, but not as economic.

Superior in what sense, if not economic, I was curious.

This is deference and ignorance. Disco suggested a Suzuki coupling. It could be a better reaction and involve more regioselectivity. I really don't know. I don't know the productivity of the patent route either.

None the less, in the patent route, the product is obtained directly from the electrophilic attack. If you are to produce a lot of this material, the patent route does look inviting to me. If you think about the patent route vs proposed synthesis, both depend upon a selective reaction of phenol. This is where the basic ortho-para direction of a phenol must be followed. It is difficult to overcome those basic chemical principles that textbooks describe.

I did not intend my question to be sarcastic or mocking. Apologies, if it came out that way.

I just thought your statement seemed thought-provoking and non-obvious to me and hence wanted to know what you meant by it. Especially, what the word "superior" could mean to a Chemist.

I could think of several interpretations: Elegant scheme? High selectivity? High conversions? Generality / wide-applicability of approach? Pure economics? Ease of Reaction conditions?

In other words, what's a "better reaction".

[orgopete]

I did not intend my question to be sarcastic or mocking. Apologies, if it came out that way.

I didn't take it that way. Again, I was giving deference to Disco's suggestion of using a Suzuki reaction. It may be better and as a generality, some longer routes may be superior, but in this case, I didn't know.