ChemicalBook CAS DataBase List 4-BENZYLOXY-3-METHOXY-BENZONITRILE

4-BENZYLOXY-3-METHOXY-BENZONITRILE synthesis

8synthesis methods

Product Name:4-BENZYLOXY-3-METHOXY-BENZONITRILE
CAS Number:52805-34-2
Molecular formula:C15H13NO2
Molecular Weight:239.27

4421-08-3 Synthesis

4421-08-3
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100-39-0
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52805-34-2
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Yield:52805-34-2 100%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20;

Steps:

C. Synthetic Procedures 4-Benzyloxy-3-methoxybenzonitrile⁵ (5)

4-Hydroxy-3-methoxybenzonitrile (3.4 g, 22.8 mmol) was dissolved in DMF (45 mL), potassium carbonate (4.73 g, 34.2 mmol) was added slowly, followed by benzyl bromide (3.0 mL, 25.1 mmol). The reaction mixture was stirred overnight at ambient temperature then brine (50 mL) solution was added. The precipitate was collected affording the title compound as a white solid (5.45 g, 100%). Mp: 81-83 °C (lit 81-83 °C ⁶); ¹H NMR (500 MHz, CDCl₃) δ: 3.91 (s, 3H, OCH₃), 5.21 (s, 2H, Ar-CH₂), 6.92 (d, 1H, ArH, J = 8.3 Hz), 7.11 (d, 1H, ArH, J = 1.9 Hz), 7.22 (dd, 1H, ArH, J = 1.9, 8.3 Hz), 7.30-7.46 (m, 5H, ArH). ¹³C NMR (125 MHz, CDCl₃) δ: 56.20, 70.89, 104.18, 113.32, 114.40, 119.23, 126.27, 127.25, 128.77, 128.80, 135.81, 149.68, 152.00. HRMS (ESI, m/z): calc’d for C₁₅H₁₄NO₂ [M+H]⁺240.1019 found: 240.1017

References:

Brocklesby, Kayleigh L.;Waby, Jennifer S.;Cawthorne, Chris;Smith, Graham [Tetrahedron Letters,2017,vol. 58,# 15,p. 1467 - 1469] Location in patent:supporting information

2426-87-1 Synthesis