4-Hydroxybenzaldehyde → 4-(1-Hydroxyprop-2-yn-1-yl)phenol

Temperature

-78 °C

To a solution of trimethylsilylacetylene (1.00 g, 10 mmol) (Aldrich) in dry THF (100 mL) under argon at −78° C. was added n-butyllithium (4.4 mL, 11 mmol, 2.5 M solution in hexanes) (Aldrich) dropwise. The reaction was stirred for 30 min at −78° C., after which time 4-hydroxybenzaldehyde (0.50 g, 4 mmol) (Aldrich) was added and the reaction was allowed to slowly warm to room temperature. A saturated solution of ammonium chloride (5 mL) was then added and the reaction was stirred at room temperature for 2 h. The solution was then diluted by the addition of 30 mL water, and THF was removed in vacuo. The product was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give clean 3-hydroxy-3-(4-hydroxyphenyl)-1-propyne which was used directly, without further purification. (Yield 501 mg, 84%).

1. temperatureto slowly warm to room temperature
2. stirringthe reaction was stirred at room temperature for 2 h
3. customwas removed in vacuo
4. extractionThe product was extracted with ethyl acetate (3×50 mL)
5. dry with materialthe combined organic layers were dried over magnesium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-97da1fcbbc974438a893158003116768

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313310B1