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Etherification of 4-hydroxybenzaldhyde with propargyl bromide; 4-(Prop-2-yn-1-yloxy)benzaldehyde

SyntheticPage 838
Submitted Jun 12, 2018, published Jun 17, 2018
Robert Smith (rbsmith@uclan.ac.uk), Karah Mason ()
A contribution from Smith Group


			Reaction Scheme: <IMG src="/images/empty.gif">Etherification of <SPAN id=csm1529313043105 class="csm-chemical-name csm-not-validated" title=4-hydroxybenzaldhyde grpid="1">4-hydroxybenzaldhyde</SPAN> with <SPAN id=csm1529313049776 class=csm-chemical-name title="propargyl bromide" grpid="2">propargyl bromide</SPAN><IMG src="/images/empty.gif">

Chemicals Used

4-Hydroxybenzaldhyde (Sigma Aldrich)

Propargyl bromide, 97%, 80% w/w in toluene (Alfa Aesar)

Procedure

A solution of 4-hydroxybenzaldhyde (3.03 g, 25 mmol), propargyl bromide (11.61g, 98 mmol), and potassium carbonate (13.55 g, 98 mmol) in acetone (250 mL) was heated at reflux for 4 h with constant stirring.  Upon cooling, the reaction mixture was transferred to a separating funnel along with distilled water (50 mL) and DCM (30 mL).  The product was extracted into the organic layer, isolated and dried over sodium sulphate.  The solvent was removed under reduced pressure to yield 4-(prop-2-yn-1-yloxy)benzaldehyde (3.26 g, 82 %) as a pale orange solid.

Author's Comments

The authors found the above synthesis to not require purification, however purification (if required) is achievable by column chromatography using petroleum ether:ethyl acetate = 9 :1.

Data

 1H NMR (300 MHz, Chloroform-d) δ 9.92 (s, 1H), 7.87 (d, J = 8.8 Hz, 1H), 7.10 (d, J = 8.7 Hz, 2H), 4.80 (d, J = 2.4 Hz, 2H), 2.58 (t, J = 2.4 Hz, 1H).  GCMS-(EI): found, [M+], m/z = 160.0, IR (cm-1): 3217.23, 2109.88, 1679.88, 1594.87, 1213.37.


Lead Reference

Zhang R., Gao H., Ren Y., Xiao Y., Hu J., Cheng X., Syntheses and Properties of mesoSubstituted Porphyrin Mesogens with Triazole Linkages and Peripheral Alkyl Chains, Chem Asian J., 2018, 13(5):536-544

Other References

Supplementary Information

1H - 5651-86-5.pdf
IR - 5651-86-5.pdf
MS - 5651-86-5.pdf

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Get structure file (.cdx, .sk2, .mol)

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

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