Uses
HYDROXYPIVALIC ACID METHYL ESTER, also known as methyl 2,2-dimethyl-3-hydroxypropionate, methyl hydroxyneovalerate, or methyl hydroxypentanoate, is an important raw material for the synthesis of liquid crystal materials, pharmaceutical intermediates, and dyes. It is widely used in saturated polyester resins, polyurethanes, plasticizers, and other fields, serving as a high-grade raw material for the production of resins, paints, and coatings. It is also a crucial intermediate in the synthesis of the herbicide isoxaflutole.
Chemical Properties
Clear colorless liquid
Uses
Kinetics of decomposition of methyl 2,2-dimethyl-3-hydroxypropionate to methyl isobutyrate and formaldehyde in a static system has been investigated
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Synthesis Reference(s)
The Journal of Organic Chemistry, 41, p. 585, 1976
DOI: 10.1021/jo00865a049
Synthesis Reference(s)
Journal of the American Chemical Society, 85, p. 1460, 1963
DOI: 10.1021/ja00893a017
General Description
Kinetics of decomposition of methyl 2,2-dimethyl-3-hydroxypropionate to methyl isobutyrate and formaldehyde in a static system has been investigated.
Synthesis
3-Hydroxy-2,2-dimethylpropionic acid (15.00 g, 127.0 mmol) was dissolved in methanol (200 mL), concentrated sulfuric acid (13.5 g, 254 mmol) was added, and the reaction was stirred under reflux conditions for 16 hours. After completion of the reaction, the reaction mixture was concentrated under vacuum, diluted with ethyl acetate (100 mL) and washed sequentially with water (2 x 50 mL), saturated aqueous sodium bicarbonate solution (50 mL), water (50 mL) and brine (50 mL). The organic phase was dried with anhydrous sodium sulfate and the organic solvent was subsequently removed under vacuum to afford methyl 3-hydroxy-2,2-dimethylpropionate (6.4 g, 57.2% yield) as a colorless liquid.1H NMR (400 MHz, DMSO-d6) δ: 3.71 (s, 3H), 3.56 (s, 2H), 2.05-2.04 (m, 1H), 1.19 ( s, 6H).
References
[1] Patent: WO2014/145023, 2014, A1. Location in patent: Paragraph 0390
[2] Bulletin de la Societe Chimique de France, 1904, vol. <3>31, p. 129
