Question

NMR for [4-(acetyloxy)-3-methoxyphenyl]methanediyl diacetate. Is this correct?

17.40 7.26 7.17 7.04 -3.87 2.35 2.14 Acid-catalyzed vanillin esterification possible product 2 (esterification of alcohol and aldehyde substituent) Simulated High Resolution Spectrum –7.40 –7.26 212- A OOCH3 G F E CEⓇ Hec. AHHH 7.4 7.0 CH 7.3 7.2 7.1 Chemical Shift A,B 13.041 6.101 11.5 10.5 9.5 8.5 7.5 6.5 5.5 4.5 Chemical Shift 3.5 2.5 1.5 0.5 -0.5 -1.5

Answer 1

ANS:

Yes Correct 4- actoxy - 3 - methoxy phenyl methanediyl diacetate product is correct.

From The NMR spectrum it is conforming correct.

The complete mechanism & confirmation of product formed find on below attached images.

Esterification of vanilline between acetic an hydride ander two conditions. 1 Acetic condition 2 Basic Condition Vanillin ( C8 HgO3). CH3 H canó KON condition under Alcoholt conc. Hasou & O-CH₂ Nach under basic Condition xield (69.9% CH3 4-acetyloxy-3-Methony Phenyl methanediy) di acetate OH 4-hydroxy-3-methoxy Benzaldehyde (vanillin) weld (50.14%) 4- formy, phenyl acetate

ome Result for Different Higuera zen atoms. ma Resu COM under acidic Condition the Product forming has Total 7 types of Hydrozen an atory ; atoms (16 (16 Hydroz Hydrozens are present). from the NMR spectrum 1H, singlet 7.40 (H) 3H, Singlet (Benzene) 7.26, 7.177.04 (E) (F (G 3.87 (c) 3 H, Singlet TH, Singlet 2.35, 2.14 (A,B) O CH3 CH & where as in Basic Condition the Product formed is having 10 hydrozen atony only, 4- formy) Phenyl acetate NMR spectrum not matching with given NMR spectrum. so the product formed is My-acetyloxy-3-methony Phenyl methanedig, diacetate is correct.