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ChemicalBook CAS DataBase List 4-(3-HYDROXY-PROPYL)-BENZONITRILE
83101-12-6

4-(3-HYDROXY-PROPYL)-BENZONITRILE synthesis

11synthesis methods
3-(4-CYANOPHENYL)PROPANOIC ACID

42287-94-5

4-(3-HYDROXY-PROPYL)-BENZONITRILE

83101-12-6

4) Synthesis of 3-(4-cyanophenyl)propanol Borane-tetrahydrofuran complex (1.0 M, 33.0 mL, 33.0 mmol, dissolved in tetrahydrofuran) was slowly added dropwise to a stirred tetrahydrofuran solution (50 mL) of 3-(4-cyanophenyl)propanoic acid (4.40 g, 25.1 mmol). The reaction mixture was stirred continuously for 14 hours at room temperature. Upon completion of the reaction, water (50 mL) and potassium carbonate (10.0 g, 72.4 mmol) were added to the mixture. Subsequently, the mixture was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 3-(4-cyanophenyl)propanol as a yellow oil (3.20 g, 79% yield). 1H-NMR (200 MHz, CDCl3) δ: 7.58 (2H, d, J = 8.2 Hz), 7.31 (2H, d, J = 8.2 Hz), 3.68 (2H, t, J = 6.2 Hz), 2.79 (2H, t, J = 7.8 Hz), 2.00-1.75 (2H, m). IR (pure): 3319, 2943, 2229, 1608, 1505, 1415, 1054, 854, 817 cm-1.

42287-94-5 Synthesis
3-(4-CYANOPHENYL)PROPANOIC ACID

42287-94-5
110 suppliers
$6.00/250mg

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Yield:83101-12-6 89.1%

Reaction Conditions:

with borane-THF in tetrahydrofuran at 20;

Steps:

20.1 1. Preparation of 4-(3-hydroxypropyl)benzonitrile

To a solution of 3-(4-cyanophenyl)propanoic acid (500.0 mg, 2.85mmol)in THF (5 mL) was added BH3-THF (1.9 mL) (2M in THF). The mixture was stirred at rt overnight. The reaction was quenched by slow addition of MeOH (2 mL). The reaction mixture was stirred for additional 30 min at 20°C. The reaction mixture was concentrated and purified by flash chromatography to give4-(3-hydroxypropyl)benzonitrile (410.0 mg, 89.1%) as a light yellow oil. LCMS (ESI) found: 162 [M+H]+.

References:

WO2022/169755,2022,A1 Location in patent:Paragraph 0308-0309

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