Novel facile method for the synthesis of methyl 2-fluoro-3-hydroxypropanoate from Claisen salts and formaldehyde in water. (2nd December 2022)

• Record Type: Journal Article
• Authors: Fu, Boqiao; Cao, Zhen; Wu, Boying; Mao, Chongyang; Qin, Caiqin; Chen, Shigui
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 197:Number 12(2022)
• Page Start: 1277
• Page End: 1283
• Publication Date: 2022-12-02
• Subjects: Methyl 2-fluoro-3-hydroxypropanoate -- Claisen salt -- water -- methyl 3-chloro-2-fluoropropanoate -- methyl 2-fluoroacrylate; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2022.2097232
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: Methyl 2-fluoro-3-hydroxypropanoate (MFHP) and its derivative methyl 3-chloro-2-fluoropropanoate (MCFP) are easily converted into methyl 2-fluoroacrylate (MFA). A roundabout strategy was put forward based on MFHP to overcome the shortcomings of MFA to extend its storage life and reduce its cost of shipment and storage. In our work, a novel and facile method for the synthesis of MFHP was developed based on Claisen salts and formaldehyde in water as followed: 37% formaldehyde aqueous (9.0 equiv.) was dropped into the aqueous of Claisen salt (1.0 equiv.) and NaHCO3 (1.0 equiv.) at room temperature for 2-3 h to obtain MFHP in yield of 81.3%. Graphical Abstract: UF0001