Methanol → 4-Ethynylbenzaldehyde

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Reaction Steps

As shown in the following Reaction 7, 250 mg (1.19 mmol) of 4-trimethylsilylethynyl benzaldehyde obtained in A of Example 1-2 was melted in 10 mL of methylenechloride and 10 mL of methanol at room temperature, and 1.25 g (9.04 mmol, 7.6 eq) of potassium carbonate was added thereto, and then the reaction solution was stirred for 6 hours. Next, the reaction solution was extracted with ether 2 times and with 1M sodium chloride aqueous solution 1 time. The organic solvent layer was dehydrated with magnesium sulfate, filtered, and then distilled under reduced pressure. The compound distilled under reduced pressure was purified with a column chromatography (mobile phase volume ratio; ethylacetate:n-hexane=1:10) to obtain 130 mg of 4-ethynylbenzaldehyde with the yield of 93%. NMR data of the obtained compound is as follows. [1H NMR (400 MHz, CDCl3): δ 10,02 (s, 1H), 7.83 (d, 2H), 7.63 (d, 2H), 3.27 (s, 1H)].

Provenance & Evidence