163164-47-4

4-(2-Hydroxyethyl)benzaldehyde is used in the synthesis of thromboxane receptor antagonists and -thromboxane synthase inhibitors based on a dioxane linkage.

General procedure for the synthesis of 4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)benzaldehyde from 4-(2-hydroxyethyl)benzaldehyde: 1. 2.8 g (11.95 mmol) of 4-[2-(tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde was dissolved in a mixture of 48 mL of 1 M hydrochloric acid and 60 mL of acetone, and the reaction was stirred for 5 hr at 5 °C. 2. Upon completion of the reaction, the reaction mixture was combined with 140 mL of saturated sodium bicarbonate solution and extracted with ethyl acetate. 3. The organic phases were combined, washed three times with water and then dried over anhydrous sodium sulfate. 4. Purification was carried out by silica gel column chromatography with the eluent cyclohexane/ethyl acetate (1:1). 5. The product 4-(2-hydroxyethyl)benzaldehyde was obtained as 1.3 g in 72.4% yield. Product characterization: C9H10O2 (M = 150.17); calculated value: molar peak (M + H)+: 151; measured value: molar peak (M + H)+: 151; Rf value: 0.52 (silica gel, petroleum ether/ethyl acetate 1:1).

[1] Patent: US2004/242572, 2004, A1. Location in patent: Page/Page column 52
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1608 - 1628