![](/CAS/GIF/1700-29-4.gif)
4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE synthesis
- Product Name:4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE
- CAS Number:1700-29-4
- Molecular formula:C16H15NO2
- Molecular Weight:253.3
![4-HYDROXY-3-METHOXYPHENYLACETONITRILE](/CAS/GIF/4468-59-1.gif)
4468-59-1
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$23.00/250 mg
![Benzyl bromide](/CAS/GIF/100-39-0.gif)
100-39-0
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![4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE](/CAS/GIF/1700-29-4.gif)
1700-29-4
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$10.00/250mg
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]
![4-BENZYLOXY-3-METHOXYBENZALDEHYDE](/CAS/GIF/2426-87-1.gif)
2426-87-1
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$8.00/5g
![4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE](/CAS/GIF/1700-29-4.gif)
1700-29-4
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$10.00/250mg
![4-BENZYLOXY-3-METHOXYBENZYL ALCOHOL](/CAS/GIF/33693-48-0.gif)
33693-48-0
65 suppliers
$18.00/1 g
![4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE](/CAS/GIF/1700-29-4.gif)
1700-29-4
88 suppliers
$10.00/250mg
![Benzyl bromide](/CAS/GIF/100-39-0.gif)
100-39-0
423 suppliers
$10.00/10 g
![4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE](/CAS/GIF/1700-29-4.gif)
1700-29-4
88 suppliers
$10.00/250mg
![Vanillin](/CAS/GIF/121-33-5.gif)
121-33-5
1093 suppliers
$9.00/1g
![4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE](/CAS/GIF/1700-29-4.gif)
1700-29-4
88 suppliers
$10.00/250mg