Regioselective Protection of the 4-Hydroxyl of 3,4-Dihydroxy-benzaldehyde

methoxybenzyl, o-nitrobenzyl, 2,6-dichloro ethane, 3,4-dichloro vinyl, and …. 2,6-dichlorobenzene. 69. 85. 80. 80. 124-125 125-126 167-168 ….

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Regioselective Protection of the 4-Hydroxyl of 3,4-Dihydroxy-benzaldehyde
The regioselective protection of the 4-hydroxyl group of 3,4-dihydroxy-benzaldehyde was accomplished with seven different protecting groups (benzyl, p-methoxybenzyl, o-nitrobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, vinyl and propargyl) in yields ranging between 67-75%
Experimental
Melting points were determined on a hot stage instrument and are uncorrected. Infrared spectra were recorded either as KBr pellets or neat on a Perkin Elmer System 2000 FTIR. 1H-NMR spectra were recorded on a Bruker AMX300 spectrometer at 300MHz and chemical shifts are expressed in ppm using TMS as internal standard. 13C-NMR spectra were recorded on a Bruker AMX300 spectrometer at 75.4MHz and chemical shifts are expressed in ppm using chloroform as internal standard. Mass spectra were recorded on a Hewlett Packard 5898B spectrometer

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