3-(4-Hydroxymethylphenoxy)propionic Acid

Abstract

[101366-61-4] C10H12O4 (MW 196.20) InChI = 1S/C10H12O4/c11-7-8-1-3-9(4-2-8)14-6-5-10(12)13/h1-4,11H,5-7H2,(H,12,13) InChIKey = WPWKJUVXEMKOHS-UHFFFAOYSA-N (acid-labile linker/handle used for solid-phase synthesis of peptide acids, and more general applications to solid-phase organic synthesis) Alternate Name: p-alkoxybenzyl (PAB) ester linker. Physical Data: mp 149–150 °C, analytically calculatedfor C10H12O4; C, 61.22; H, 6.17. Found: C, 61.08; H, 6.19. Solubility: soluble in most polar organic solvents. Form Supplied in: the title compound is a crystalline solid. The title compound and variations can be obtained on-resin with or without anchored protected amino acid moieties. See main text for further details. Analysis of Reagent Purity: NMR, elemental analysis, TLC, or other chromatographic criteria. Preparative Methods: it can be prepared by alkylation of 4-hydroxybenzaldehyde with 3-bromopropionic acid, followed by NaBH4 reduction of aldehyde to alcohol. Purification: recrystallization from minimal MeOH–EtOAc (1:1), adding chilled pentane. Handling, Storage, and Precautions: routine procedure is followed. Details depend on whether materials are solid organic compounds, are attached to a solid support, and/or include protected amino acid moieties. If possible, materials should be refrigerated to increase shelf life. Disposal: these materials are not particularly hazardous, and standard methods for solid organic waste disposal should be adequate.