Back to Search Start Over

Syntheses of Stable Isotope [13C]/D Labelled p-Methoxybenzoic Acid

Syntheses of Stable Isotope [13C]/D Labelled p-Methoxybenzoic Acid

Authors :
WANG Wei;DU Xiaoning;XU Jianfei;LEI Wen
Source :
Journal of Isotopes, Vol 33, Iss 6, Pp 235-240 (2020)
Publication Year :
2020
Publisher :
Editorial Board of Journal of Isotopes, 2020.

Abstract

Stable isotope labelled p-methoxybenzoic acid is an important intermediate in the synthesis of stable isotope labelled preservative, anti-microbial, anti-fungal, spices, and other internal standard reagentsspices, drugs and other compounds. A new procedure for the synthesis of the [13C]/D labelled p-methoxybenzoic acid has been developed in this paper. The stable isotope [13C]/D labelled p-methoxybenzoic acid was synthesized from ethyl paraben and [13C]/D labelled iodomethane (13CH3I or CD3I) under alkaline conditions via two steps. In this paper, the optimal reaction temperature, molar ratio, and reaction time were obtained by single factor experiment. The optimal reaction conditions were obtained as follows, the reaction temperature was 80 ℃, the molar ratio of [13C]/D labelled iodomethane to ethyl paraben was 1.15∶1, the reaction time was 6 h. In the optimization conditions, the yield of [13C] labelled p-methoxybenzoic acid was 91.12%, and the utilization of 13CH3I was 79.32%. The melting point of product was 186.5~187.8 ℃. The product analyses were made with LC-MS, the chemical purity was 99.1%, and the isotopic abundance was 99.0 atom%13C. The qualitative analysis of product was confirmed by 1H NMR. By the same technological conditions, the stable isotope [D] labelled p-methoxybenzoic acid was synthesized from ethyl paraben and [D] labelled iodomethane (CD3I). The yield of [D] labelled p-methoxybenzoic acid was 90.49%, and the utilization of CD3I was 78.70%, and the melting point of product was 186.3~188.1 ℃. The product analyses were made with LC-MS, the chemical purity was 99.0%, and the isotopic abundance was 98.1 atom%D. The qualitative analysis of product was confirmed by 1H NMR.

Details

Language :
Chinese
ISSN :
10007512
Volume :
33
Issue :
6
Database :
Directory of Open Access Journals
Journal :
Journal of Isotopes
Publication Type :
Academic Journal
Accession number :
edsdoj.bcc8f793239648cba7fcad48c1d099f6
Document Type :
article
Full Text :
https://doi.org/10.7538/tws.2018.31.04.0235