p-Toluenesulfonic acid → 2-Nitro-6-(tetrahydropyran-2-yloxy)phenol

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Reaction Steps

0.030 g of p-toluenesulphonic acid and 17.8 g of 3,4-dihydro-2H-pyrane are added to a mixture of 29.8 g of 2,3-dihydroxy-nitrobenzene in 400 ml of absolute benzene and the solution is left to stand for 7 days at 20°. It is filtered through 15 g of a silica gel formulation (Merck silica gel 60; grain size 0.063-0.200 mm) and the silica gel is rinsed with benzene. After distilling off the benzene under reduced pressure, a reddish oil is obtained which, when crystallised from hexane, gives 2-hydroxy-3-(tetrahydropyran2-yloxy)-nitrobenzene in the form of yellow crystals; melting point 72°-73°.

Provenance & Evidence