1-Propanethiol, sodium salt (1:1) → 4-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

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Reaction Steps

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (22 g, 98 mmol) was dissolved in DMF (490 mL) and sodium propanethiolate (12.5 g, 127 mmol) was added. The mixture was brought to 100° C. and the reaction mixture was stirred for 30 minutes. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in dichloromethane (200 mL) and saturated aqueous ammonium chloride (200 mL). Hydrochloric acid 1N was then added until acidic pH. The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to yield 20 g (quantitative yield) of the desired product as a yellow oil, used in the next step without further purification.

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