The reaction of cyclohexanone (1) and N,N-dimethylamine (2) with (i) sodium triacetoxyborohydride (NABH(OAc)3) in methanol with acetic acid (ACOH) affords N,N- dimethylcyclohexanamine (3) in high yield. However, if anhydrous HCI is used (ii), the reaction yield of (3) is low and a side reaction occurs to produce alcohol (4). i. NaBH(OAc)3 ii. NaBH(OAc)3 OH Acetic acid, methanol HCI, Methanol 95% yield Low yield 2 3 4.

The reaction of cyclohexanone (1) and N,N-dimethylamine (2) with (i) sodium triacetoxyborohydride (NABH(OAc)3) in methanol with acetic acid (ACOH) affords N,N- dimethylcyclohexanamine (3) in high yield. However, if anhydrous HCI is used (ii), the reaction yield of (3) is low and a side reaction occurs to produce alcohol (4). i. NaBH(OAc)3 ii. NaBH(OAc)3 OH Acetic acid, methanol HCI, Methanol 95% yield Low yield 2 3 4.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.47P: The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii...

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