3,3-Dimethylacrylic acid CAS#: 541-47-9

3,3-Dimethylacrylic acid

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3,3-Dimethylacrylic acid Basic information

3,3-Dimethylacrylic acid Chemical Properties

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3,3-Dimethylacrylic acid Usage And Synthesis

DescriptionMay be prepared by the action of alkalis or bases on the ester of α-bromoisovaleric acid; by condensation of acetone with malonic acid or bromoacetic ester; by oxidation of mesityl oxide with sodium hypochlorite.
Chemical Properties3-Methylcrotonic acid has green, phenolic, dairy aroma
Chemical PropertiesWhite to brown crystal
OccurrenceReported found in the rhizomes of Senecio kaempferi Seib.; the corresponding ester occurs naturally in waste wort. Also reported found in raspberries, wheat bread, cocoa, coffee, black tea, Arctic bramble, and green and roasted maté.
DefinitionChEBI: A methyl-branched fatty acid that is but-2-enoic acid bearing a methyl substituent at position 3.
PreparationBy the action of alkalis or bases on the ester of α-bromoisovaleric acid; by condensation of acetone with malonic acid or bromoacetic ester; by oxidation of mesityl oxide with sodium hypochlorite.
Synthesis Reference(s)Journal of the American Chemical Society, 71, p. 3214, 1949 DOI: 10.1021/ja01177a079
Organic Syntheses, Coll. Vol. 3, p. 302, 1955
Tetrahedron Letters, 36, p. 2469, 1995 DOI: 10.1016/0040-4039(95)00285-K
Purification MethodsCrystallise the acid from hot water or pet ether (b 60-80o). [Beilstein 2 IV 1555.]

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