ChemicalBook CAS DataBase List Benzocaine

Benzocaine synthesis

11synthesis methods

Product Name:Benzocaine
CAS Number:94-09-7
Molecular formula:C9H11NO2
Molecular Weight:165.19

Benzocaine is the ethyl ester of 4-aminobenzoic acid (2.3.1). The classic, optimal way of benzocaine synthesis is the reduction of the nitro group of the ethyl ester of 4-nitrobenzoic acid to benzocaine by hydrogen, which generates directly in the reaction medium by the reaction of iron filings with dilute acids [24–26].

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Yield:94-09-7 100%

Reaction Conditions:

with hydrogen in methanol at 20; under 760.051 Torr; for 6 h;chemoselective reaction;Reagent/catalyst;

Steps:

4.4 General procedure for the hydrogenation

General procedure: A mixture of the substrate (0.250mmol) and catalyst [8% Pd/CR11 (3.3mg, 2.50μmol) or 9% Pd/CR20 (3.0mg, 2.50μmol)] in MeOH (1mL) was stirred under an H₂ atmosphere (balloon) at room temperature. After a specific time, the mixture was filtered through a membrane filter (0.45 or 0.2μm), and the filtrate was concentrated in vacuo to give the corresponding spectrometrically-pure reduced product. If the reaction was not completed, the temperature was raised to 40 or 50°C. If the reaction was still incomplete, the H₂ pressure was increased to 3 or 5atm. All the products were known, and the ¹H NMR spectral data of the products were identical to those in the literature (see Supplementary data).

References:

Monguchi, Yasunari;Ichikawa, Tomohiro;Nozaki, Kei;Kihara, Kensuke;Yamada, Yuuko;Miyake, Yutaka;Sawama, Yoshinari;Sajiki, Hironao [Tetrahedron,2015,vol. 71,# 37,art. no. 26568,p. 6499 - 6505] Location in patent:supporting information

64-17-5 Synthesis