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Etherification of 4-Hydroxybenzaldehyde with a benzyl bromide; 4-(4-Nitrobenzyloxy)benzaldehyde

SyntheticPage 836
DOI: 10.1039/SP836
Submitted Jun 08, 2018, published Jun 09, 2018
Robert Smith (rbsmith@uclan.ac.uk), Megan Critchley (MCritchley2@uclan.ac.uk)
A contribution from Smith Group


			Reaction Scheme: <IMG src="/images/empty.gif"><IMG alt="" src="/images/empty.gif">Etherification of <SPAN id=csm1528706650521 class="csm-chemical-name csm-not-validated" title=4-Hydroxybenzaldehyde>4-Hydroxybenzaldehyde</SPAN><SPAN style="BACKGROUND-COLOR: transparent"> with a benzyl bromide</SPAN><IMG alt="" src="/images/empty.gif"><IMG src="/images/empty.gif">

Chemicals Used

4-Hydroxybenzaldehyde (Sigma Aldrich)

4-nitrobenzyl bromide (Sigma Aldrich)

Potassium carbonate (Sigma Aldrich)

DMF (Sigma Aldrich)

Procedure

A solution of 4-hydroxybenzaldhyde (2.0 g, 16.4 mmol), 4-nitrobenzyl bromide (3.54 g, 16.4 mmol), potassium carbonate (3.40 g, 24.6 mmol) in dry DMF (20 mL) was heated at 100℃ for 3 h with constant stirring. The reaction mixture was allowed to cool, added to ice water and the resulting precipitate was isolated at the pump to give a yellow solid. The solid was washed three times with water (10 mL each time) to yield 4-(4-nitrobenzyloxy)benzaldehyde (3.11 g, 74%) as a light yellow solid. [How was it dried?]

Author's Comments

The title compound can be recrystallized either using 1:1 mixture of hexane : toluene [please give brief protocol] or purified by column chromatography on silica gel using n-hexane/EtOAc mixture as a solvent system.  The authors found the above synthesis to not require purification, as the compound produced was sufficiently pure to act as an intermediate for the next stage of the synthesis.

Data

1H NMR (300 MHz, DMSO-d6) δ 9.88 (s, 1H), 8.27 (d, J = 8.7 Hz, 2H), 7.89 (d, J = 8.7 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 7.23 (d, J = 8.7 Hz, 2H), 5.41 (s, 2H).  13C NMR (75 MHz, DMSO) δ 191.83, 163.25, 147.56, 144.66, 132.32, 130.50, 128.85, 124.15, 115.78, 68.83. MS m/z: 257.22 [M+]. IR (cm-1): 3060.96, 2926.67, 1686.57, 1595.79, 1160.45.


Lead Reference

Kafle, B., Aher, NG., Khadka, D., Park, H., Cho, H. Isoxazol-5(4H)one Derivatives as PTP1B Inhibitors Showing an Anti-Obesity Effect, Chem Asian J., 2011, 6(8):2073-9

Supplementary Information

1H NMR (1H - 67565-48-4.pdf)
13C NMR (13C - 67565-48-4.pdf)
135-DEPT NMR (135-DEPT - 67565-48-4.pdf)
13C vs 135-DEPT (13C vs 135-DEPT - 67565-48-4.pdf)
HSQC - NMR (HSQC - 67565-48-4.pdf)
IR (IR - 67565-48-4.pdf)
1H 1H COSY - NMR (1H 1H COSY - 67565-48-4.pdf)

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Keywords: aldehydes, alkyl/alkenyl/aryl halides, aromatics/arenes, substitution

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