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Old Jan 6th 2016, 07:49 PM   #1
JediMaster
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Question Troubles with organic synthesis of sulfo derivatives


I know that D is methylbenzene.
Also they say in the task, that sulfonation of d gives two isomers, and the reactions further are conducted upon the main isomer.
I think it is para-sulfotoluene, because of steric reasons.
Next simple chlorination, and oxidation of side chain alkyl group (methyl)
and G is 2-chloro-4-sulfobenzoic acid
And that is when the trouble begins:
I don't know what happens next.
I know that carboxylic acid chloride can be synthesized only with SOCl2
So may be there will be chlorination of sulfo group and the water will just remove it? and finally we will have ortho-chlorobenzoic acid?
If am not right, where i have a mistake?
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