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ChemicalBook CAS DataBase List cis-4-Aminocyclohexanecarboxylic acid
3685-23-2

cis-4-Aminocyclohexanecarboxylic acid synthesis

2synthesis methods
4-Aminobenzoic acid

150-13-0

4-AMINOCYCLOHEXANECARBOXYLIC ACID

1776-53-0

cis-4-Aminocyclohexanecarboxylic acid

3685-23-2

The general procedure for the synthesis of 4-aminocyclohexanecarboxylic acid and cis-4-aminocyclohexanecarboxylic acid from p-aminobenzoic acid is as follows: p-aminobenzoic acid (10.0 g, 0.07 mol, 1 eq.), 5% Ru/C catalyst (2.50 g), and 10% NaOH solution (100.0 mL) were added in an autoclave. The mixture was stirred to react under 100 bar hydrogen pressure and 15 bar hydrogen atmosphere. After 20 hours of reaction, the progress of the reaction was detected by thin layer chromatography (TLC), the unfolding agent was dichloromethane/methanol/ammonia (5:5:1, v/v/v), and the staining agent was ninhydrin to confirm that the starting material was completely consumed. Nuclear magnetic resonance (NMR) analysis showed that the reaction was fully converted and the ratio of cis to trans product was 1:4.6. After confirming that the reaction was complete, the reaction was stopped.

-

Yield:-

Steps:

Multi-step reaction with 2 steps
1: H2SO4 / Heating
2: (i) H2, Raney-Ni, EtOH, (ii) KOH

References:

Schneider,W.;Dillmann,R. [Chemische Berichte,1963,vol. 96,p. 2377 - 2386]

FullText

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