Alkoxyacetic acid

A 2-alkoxyethanol with a fluorine-containing alkoxy group can be selectively oxidized by nitric acid to the 2-alkoxyacetic acid without cleavage of the ether bond, e.g. oxidation of 9 to 10.148... 

Chloroacetic Acid (ClCHiCOOHf. [CAS 79-11-8 J. Chloroacelic acid can be synthesized by the radical chlorination of acetic acid, treatment of trichloroethylene with concentrated H S04. oxidation of 1.2-dichloro ethane or chloroaceialdehyde. amine displacement from glycine, or chlorination of ketene. It behaves as a very strong monobasic acid and is used as a strong acid catalyst for diverse reactions. The Cl function can be displaced in base-catalyzed reactions. For example, it condenses with alkoxides to yield alkoxyacetic acids CICH COOH... 

The photodecarboxylation of alkoxyacetic acids in the presence of HgO and iodine has been studied.Karauchi et al. have studied the photodecarboxylation of the Schilf base (117). Low-temperature matrix isolation techniques have been used to trap and study the pyranone (118) obtained by the decarboxylation of the dilactone (119). Photodecarboxylation of the carbamates (120) in acetonitrile provides a simple route to the azabicyclobutanes (121). ... 

Photodecarboxylation of pyruvic acid (135) in the gas phase has been examined using i.r. fluorescense spectroscopy. The reaction is thought to proceed via the intermediate hydroxycarbene (136) which undergoes isomerization to ethanal (137). An analogous five-centred mechanism has been proposed to account for photoelimination of carbon dioxide from acrylic and methacrylic acids. Photodecarboxylation of alkoxyacetic acids has been observed in the presence of mercury(u) oxide and iodine and yields alkoxyalkyl alkoxyacetates via alkoxyalkyl iodide intermediates. ... 

Laitinen J, Liesivuori J, Savolainen H. Urinary alkoxyacetic acids and renal effects of exposure to ethylene glycol ethers. Occup Environ Med 1996 53(9) 595-600. 

The alkoxyacid metabolites appear to be responsible for the toxic effects reported in the testes, bone marrow, and embryo. The testes, bone marrow, and embryo contain large numbers of rapidly dividing and differentiating cells, and it is possible that one or more processes of cell division and differentiation are affected. It has been hypothesized that alkoxyacetic acids may be introduced into the Krebs cycle by formation of methoxy- or ethoxyacetyl-CoA and by formation of methoxy- or ethoxycitrate by mitochondrial enzymes. 

Ghanayem BI, Burka LT, Matthews HB. 1989. Structure-activity relationships for the in vitro hematotoxicity of n-alkoxyacetic acids, the toxic metabolites of glycol ethers. Chem-Biol Interact 70 339-352. 

Groeseneken D, Veulemans H, Masschelein R, et al. 1989. An improved method for the determination in urine of alkoxyacetic acids. Int Arch Occup Environ Health 61 249-254. 

Diastereo- and Enantioselective Aldol Reactions. Optically active 1,2-diol units are widely distributed in natural products such as macrolides, polyethers, and carbohydrates, etc. The aldol reactions of the enolates derived from a-alkoxyacetic acid ester derivatives with aldehydes provide a useful way to construct 1,2-diols, and several as)unmetric reactions have been developed. 

Apart from modified silica gel, the most frequently used solid-phase adsorbents are activated charcoal, macroreticular resins (XAD), ordinary silica gel, aluminum oxide, and Florisil. Activated charcoal is a universal adsorbent for concentrating trace organic materials in aqueous solutions and air, XAD resins are also commonly employed for extracting organic trace constituents, such as alkoxyacetic acids [1.57], organochlorine pesticides [200], [218], carbamates [198], 202j, and triaz.ines [218] from aqueous matrices. 

Domingo LR, Pichta- MT, Safont VS, Andres J, Chuchani G (1999) Theoretical study of the mechanisms for the alkoxyacetic acids decomposition. J Phys Chem A 103 3935-3943... 

Chapter 13. Compounds Derived from Alkoxyacetic Acids [5958] p. 1321... 

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