Etherification of 4-hydroxybenzaldhyde with propargyl bromide; 4-(Prop-2-yn-1-yloxy)benzaldehyde
SyntheticPage 838
DOI:
10.1039/SP838
Submitted Jun 12, 2018, published Jun 17, 2018
Robert Smith (
rbsmith@uclan.ac.uk), Karah Mason (
)
A contribution from
Smith Group
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 meso‐Substituted 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.pdfIR - 5651-86-5.pdfMS - 5651-86-5.pdf
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Keywords: aldehydes, alkyl/alkenyl/aryl halides, aromatics/arenes, ethers, substitution
