DOI: 10.14469/hpc/8136 Metadata

Created: 2021-04-26 15:02

Last modified: 2021-04-30 10:26

Author: Wei Xin Chua

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

4-dimethylaminopyridine(DMAP) (0.1 g, 0.5 mmol) and EDC.HCl (1.2 g, 6.5 mmol) were added to acetonitrile(15 mL). trans-4-methyl-1-cyclohexanecarboxylic acid (0.7 g, 5 mmol, in 8 mL acetonitrile) and acetovanillinone (0.8 g, 5 mmol, in 10.5 mL acetonitrile) were added to the resultant mixture. The mixture was heated under reflux and the progress of the reaction was monitored by thin layer chromatography. After refluxing for 2.5 h, hexane (20 mL) was added and the resultant mixture was washed with 1M hydrochloric acid (2 x 20 mL). As white precipitate was observed, the mixture was washed with 10 mL ethyl acetate, before washing with 10 wt% sodium bicarbonate (2 x 20 mL) and subsequently with 20 mL distilled water. As white precipitate was observed once more, the resultant mixture was washed with 20 mL ethyl acetate before washing with saturated aqueous sodium chloride (2 x 20 mL). The separated organic phase was dried (MgSO4) and filtered under gravity. MgSO4 was rinsed with 10 mL ethyl acetate and the rinsings were transferred to the filtrate. Volatiles were removed in vacuo to give a white powder (1.0 g, 3.4 mmol, 67% yield). 1H NMR (400 MHz, CDCl3) δH 7.57 (1H, d, J = 2.0 Hz), 7.53 (1H, dd, J = 2.0, 8.0 Hz), 7.08 (1H, d, J = 8.4 Hz), 3.85 (3H, s), 2.58 (3H, s), 2.50 (1H, tt, J = 3.2, 12.4 Hz), 2.13 (2H, dd, J = 2.8, 14.4 Hz), 1.80 (2H, dd, J = 3.2, 14.0 Hz), 1.55 (4H, td, J = 3.2, 12.4 Hz), 1.43 - 1.36 (1H, m), 1.00 (2H, qd, J = 3.2, 13.2 Hz), 0.91 (3H, d, J = 6.8 Hz) ppm; IR (ATR, neat) νmax/cm-1 1751 (s, C=O), 1122 (s, C-O)

Files

Filename	Size	Type	Description
4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate.mnova	466KB	chemical/x-mnova	Analysed NMR data (mnova file)
4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate.mnpub	0	chemical/x-mnpub	Mestrenova signature file for 4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate.mnova
4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate.jdx	186KB	chemical/x-jcamp-dx	NMR data (JCAMP file)
4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate.pdf	27KB	application/pdf	NMR spectrum (PDF file)
4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate.cdxml	6KB	chemical/x-cdxml	Molecular structure (ChemDraw)
NMR data.zip	1MB	application/zip	Raw NMR data (zip file)
NMR data.mnpub	0	chemical/x-mnpub	Mestrenova signature file for NMR data.zip

Member of collection / collaboration

DOI	Description
10.14469/hpc/7350	1st Year undergraduate synthesis 1.2 laboratory (2020-2021)

Subject Keywords

Keyword	Value
inchi	InChI=1S/C17H22O4/c1-11-4-6-13(7-5-11)17(19)21-15-9-8-14(12(2)18)10-16(15)20-3/h8-11,13H,4-7H2,1-3H3
inchikey	VLPKWXAYAYMWRB-UHFFFAOYSA-N

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