5-formyl-2-methoxyphenyl cyclohexanecarboxylate

DOI: 10.14469/hpc/8000 Metadata

Created: 2021-03-19 15:36

Last modified: 2021-03-22 12:53

Author: Colin Chow

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

Isovanillin (0.005 mol, 0.7 g) was added to cyclohexanecarboxylic acid (0.0055 mol, 0.8 g) and dissolved in 34 mL acetonitrile with 1.1 g EDC.HCl and 0.0611 g DMAP. Reaction flask was heated under reflux for one hour. 20 mL hexane was added to mixture, then washed with 1 M aqueous HCl 20 mL x2, 10%wt aqueous sodium bicarbonate 20 mL x2, distilled water 20 mL x1, brine 20 mL x2, and dried using MgSO4. Mixture was filtered under gravity and solvent removed by rotary evaporation. Further workup was performed on aqueous layer by extraction into 70 mL ethyl acetate, washing with brine 20 mL, drying with MgSO4 and solvent removal by rotary evaporation. Product was a white, crystalline solid: 0.8 g (61.1%). 1H NMR (400 MHz, CDCl3): δ = 9.85 (s, 1H, CHO), 7.735 (dd, 1H, 3J = 8.5 Hz, 4J = 2.0 Hz, Ar-H), 7.555 (d, 1H, 4J = 2.0 Hz, Ar-H), 7.055 (d, 1H, 3J = 8.5 Hz, Ar-H), 3.89 (s, 3H, OCH3); IR (ATR): ν (cm-1) = 2937 (C-H), 2917, 2849, 1749, 1676 (C=O), 1605, 1578, 1509, 1457, 1438, 1392, 1331, 1318, 1278, 1258, 1206, 1182, 1162, 1117, 1098, 1065, 1020, 979, 961, 922, 896, 878, 826, 801, 788, 725, 669, 635, 587, 573, 558, 532, 520, 472, 440, 419, 410.

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ccc20_PROTON-1-1.jdf 550KB chemical/x-jeol-jdf Raw data JDF
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Syn1.2NMR.pdf 43KB application/pdf Spectrum PDF
ccc20.cdxml 6KB chemical/x-cdxml Chemdraw XML

Member of collection / collaboration

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

Subject Keywords

KeywordValue
inchi InChI=1S/C15H18O4/c1-18-13-8-7-11(10-16)9-14(13)19-15(17)12-5-3-2-4-6-12/h7-10,12H,2-6H2,1H3
inchikey OIOFXYWJPMDDHA-UHFFFAOYSA-N

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