An Investigation into the Regioselectivity of the Acid Catalysed Claisen Rearrangement of Methyl 4- and 5-Allyloxy-2-hydroxybenzoate and Derivatives
The observed products from the acid catalysed Claisen rearrangement of the methyl esters (1c-g) indicate that, unlike the thermal reaction, regiochemical control is independent of internal hydrogen bonding.
Harwood, Laurence M.
p. 530 - 532
(2007/10/02)
Trifluoroacetic Acid Catalysed Claisen Rearrangement of 5-Allyloxy-2-hydroxybenzoic Acid and Esters: an Efficient Synthesis of (+/-)-Mellein
5-Allyloxy-2-hydroxybenzoic acid (1a) and the esters (1b - f) in refluxing trifluoroacetic acid are smoothly converted into 3,4-dihydro-5,8-dihydroxy-3-methylisocoumarin (3) and the corresponding 4-alkoxycarbonyl-2,3-dihydro-5-hydroxy-2-methylbenzofurans (4a - f) via regioselective Claisen rearrangement to the 6-position of the aromatic nucleus with subsequent acid catalysed cyclisation.
Harwood, Laurence M.
p. 1120 - 1122
(2007/10/02)
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