DOI: 10.14469/hpc/10195 Metadata

Created: 2022-03-08 12:54

Last modified: 2022-03-09 17:38

Author: Tianyue Chen

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

4-ethylguaiacol (0.76 g, 5.0 mmol) and arachidic acid (1.72 g, 5.5 mmol) were allowed to react with presence of acetonitrile (25 mL, 0.5 mol), 4-(dimethylamino) pyridine (DMAP) (0.06 g, 0.5 mmol) and EDC.HCl (1.25 g, 6.5 mmol). The resulting mixture was stirred and heated at 92°C until the reaction completed as shown by the results from Thin-layer chromatography. The organic layer was separated by aqueous/organic workup, where hexane (20 mL), 1M aqueous HCl (2*20 mL), 10 wt% sodium bicarbonate (2*20 mL)were added separately to the mixture and the aqueous layer formed every time collected in a conical flask, washed by water (20 mL) and saturated sodium chloride (2×20 mL), dried (MgSO4), and evaporated to afford a colourless oil. This oil solidified under room temperature, turning into a white solid: 1.49 g (67%). M.P. 48.4 – 49.1 d = 6.94 (1H, d, J = 8.0 Hz), 6.80 (2H, m, 1J = 8.0 Hz, 2J=4.0 Hz), 3.82 (3H, s), 2.66 (2H, q, J = 8.0 Hz), 2.58 (2H, t, J = 6.0 Hz), 1.79 (2H, p, J = 8.0 Hz), 1.44 (4H, m), 1.34 (6H, J = 12.0 Hz), 1.30 (19H, s), 1.27 (6H, t), 0.92 (3H, t, J = 8.0 Hz). IR: v (cm-1) = 2955, 2915, 2870 and 2848 (s, CH), 1744 (s, C=O), 1510, 1469, 1450, 1411 (s, CO), 1335, 1304, 1270, 1241, 1227, 1200, 1146, 1118, 1104, 1035, 916, 896, 844, 718, 631, 541, 504, 466, 409.

Files

Filename	Size	Type	Description
nmr.mnova	755KB	chemical/x-mnova
nmr.mnpub	0	chemical/x-mnpub	Mestrenova signature file for nmr.mnova
nmr.jdx	298KB	chemical/x-jcamp-dx
nmr.pdf	47KB	application/pdf
4-ethyl-2-methoxyphenyl icosanoate.cdxml	7KB	chemical/x-cdxml
4th Feb NMR.zip	35MB	application/zip
4th Feb NMR.mnpub	0	chemical/x-mnpub	Mestrenova signature file for 4th Feb NMR.zip

Member of collection / collaboration

DOI	Description
10.14469/hpc/8679	1st Year undergraduate synthesis 1.2 laboratory (2021-2022)

Subject Keywords

Keyword	Value
inchi	InChI=1S/C29H50O3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-29(30)32-27-24-23-26(5-2)25-28(27)31-3/h23-25H,4-22H2,1-3H3
inchikey	APWYDNFAGXKBCO-UHFFFAOYSA-N

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