Methanol → 6,8-Di-t-butyl-2-hydroxycarbonylchroman

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Reaction Conditions

Reaction Steps

To a toluene solution (183.0 g, 0.2 mol) of 6,8-di-t-butyl -2-butoxycarbonylchroman obtained in Example 2 were added 10% aqueous sodium hydroxide solution (120.0 g, 0.3 mol) and methanol (120 g), and the mixture was stirred while heating at 70° C. for 2 h. Toluene was added to the reaction mixture and the mixture was stirred and allowed to stand, and methanol and the like were removed from the aqueous layer. After the removal, aqueous sulfuric acid solution was added to the aqueous layer, and the mixture was extracted with toluene. The extract was concentrated under reduced pressure. The residue was quantitatively analyzed by liquid chromatography according to the internal standard method. As a result, 6,8-di-t-butyl-2-hydroxycarbonylchroman was obtained in a yield of 98% [net 56.92 g, 0.196 mol]. The 1H-NMR data of the obtained 6,8-di-t-butyl-2-hydroxycarbonylchroman are shown below.

Provenance & Evidence