ChemicalBook CAS DataBase List 4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE

4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE synthesis

11synthesis methods

Product Name:4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE
CAS Number:1700-29-4
Molecular formula:C16H15NO2
Molecular Weight:253.3

4468-59-1 Synthesis

4468-59-1
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100-39-0
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1700-29-4
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Yield: 100%

Reaction Conditions:

Stage #1:4-hydroxy-3-methoxyphenylacetonitrile with potassium carbonate in acetone for 0.166667 h;
Stage #2:benzyl bromide in acetone for 4 h;Reflux;

Steps:

7 7.3.7
4-(Benzyloxy)-3-methoxyphenylacetonitrile (11)

The title compound was prepared according to a modified procedure of Imbri et al.
¹²
To a solution of 4-hydroxy-3-methoxyphenylacetonitrile (10, 1.08 g, 6.60 mmol, 1.0 eq.) in acetone (14 mL), K₂CO₃ (1.10 g, 7.92 mmol, 1.2 eq.) was added.
The suspension was stirred for 10 min.
Subsequently, benzyl bromide (1.24 g, 7.26 mmol, 1.1 eq.) was added dropwise with a syringe.
The reaction mixture was heated to reflux for 4 h.
The suspension was filtered with suction the precipitated solid was washed with acetone (10 mL).
The filtrate was concentrated under reduced pressure, the remaining solution was diluted with DCM (50 mL).
The organic layers were washed with 2 N NaOH (30 mL), brine (30 mL) and dried over Na₂SO₄.
The solvent was removed in vacuo to furnish the title compound as a yellow solid (1.67 g, 6.59 mmol, quant.).
Yield: 1.67 mg (6.59 mmol, 100 % Lit.).
Rf = 0.43 (cyclohexane/ethyl acetate, 2:1).
Mp: 65-66 °C.
¹H NMR, COSY, NOESY (400 MHz, CDCl₃): δ = 7.44-7.29 (m, 5H, Ph), 6.86 (d, ³J = 8.2 Hz, 1H, 5-H), 6.84 (d, ⁴J = 2.1 Hz, 1H, 2-H), 6.78 (dd, ³J = 8.2 Hz, ⁴J = 2.1 Hz, 1H, 6-H), 5.15 (s, 2H, PhCH₂O), 3.90 (s, 3H, OCH₃), 3.68 (s, 2H, ArCH₂CN) ppm.
¹³C NMR (100.6 MHz, CDCl3): δ = 150.2 (Cq-3), 148.0 (Cq-4), 136.9 (Cq-1, Ph), 128.7 (CH-3, CH-5, Ph), 128.0 (CH-4, Ph), 127.3 (CH-2, CH-6, Ph), 122.8 (Cq-1), 120.3 (CH-6), 118.2 (CN), 114.4 (CH-2), 111.6 (CH-5), 71.2 (PhCH₂O), 56.2 (OCH₃), 23.3 (ArCH₂CN) ppm.
The spectroscopic data matched those reported in the literature.
⁴²

References:

Colligs, Vanessa;Hansen, Steven Peter;Imbri, Dennis;Seo, Ean-Jeong;Kadioglu, Onat;Efferth, Thomas;Opatz, Till [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 22,p. 6137 - 6148]

2426-87-1 Synthesis