Methyl pivalate

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Methyl pivalate
MePivalate.png
Names
Preferred IUPAC name
Methyl 2,2-dimethylpropanoate
Other names
Methyl trimethylacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.055 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-959-1
PubChem CID
UNII
  • InChI=1S/C6H12O2/c1-6(2,3)5(7)8-4/h1-4H3
    Key: CNMFHDIDIMZHKY-UHFFFAOYSA-N
  • CC(C)(C)C(=O)OC
Properties
C6H12O2
Molar mass 116.160 g·mol−1
AppearanceColorless liquid
Odor Vinegar-Like
Density 0.873 g/cm3
Boiling point 101 °C (214 °F; 374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methyl pivalate is an organic compound with the formula CH3O2CC(CH3)3. It is a colorless liquid, the methyl ester of pivalic acid. The ester is well known for being resistant to hydrolysis to the parent acid. Hydrolysis can be effected with a solution of trimethylsilyl iodide in hot acetonitrile followed by aqueous workup. [1] [2]

Related Research Articles

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an acid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

Demethylation is the chemical process resulting in the removal of a methyl group (CH3) from a molecule. A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen atoms.

Sulfonate

A sulfonate is a salt or ester of a sulfonic acid. It contains the functional group R-SO
3
, where R is an organic group. Sulfonates are the conjugate base of sulfonic acids. Sulfonates are generally stable in water, non-oxidizing, and colorless. Many useful compounds and even some biochemicals feature sulfonates.

Dipeptide

A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiologically important, and some are both physiologically and commercially significant. A well known dipeptide is aspartame, an artificial sweetener.

Acetic anhydride Chemical compound

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Formate Salt or ester of formic acid

Formate is the anion derived from formic acid. A formate (compound) is a salt or ester of formic acid.

Acetyl chloride Chemical compound

Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

The Monsanto process is an industrial method for the manufacture of acetic acid by catalytic carbonylation of methanol. The Monsanto process has largely been supplanted by the Cativa process, a similar iridium-based process developed by BP Chemicals Ltd which is more economical and environmentally friendly.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

Trimethylsilyl chloride Chemical compound

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

Ortho ester

In organic chemistry, an ortho ester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC(OR′)3. Orthoesters may be considered as products of exhaustive alkylation of unstable orthocarboxylic acids and it is from these that the name 'ortho ester' is derived. An example is ethyl orthoacetate, CH3C(OCH2CH3)3, more correctly known as 1,1,1-triethoxyethane.

Methyl bisulfate Chemical compound

Methyl bisulfate is a chemical compound with the molecular formula CH4O4S. This compound is the mono-methyl ester of sulfuric acid. The significance of methyl bisulfate is that it is an intermediate in the hydrolysis of the important reagent dimethyl sulfate, (CH3)2SO4:

Dimethyl oxalate Chemical compound

Dimethyl oxalate is the organic compound with the formula (CO2CH3)2. It is the dimethyl ester of oxalic acid. Dimethyl oxalate is a colorless or white solid that is soluble in water.

Methyltrichlorosilane Chemical compound

Methyltrichlorosilane, also known as trichloromethylsilane, is an organosilicon compound with the formula CH3SiCl3. It is a colorless liquid with a sharp odor similar to that of hydrochloric acid. As methyltrichlorosilane is a reactive compound, it is mainly used a precursor for forming various cross-linked siloxane polymers.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

The Taft equation is a linear free energy relationship (LFER) used in physical organic chemistry in the study of reaction mechanisms and in the development of quantitative structure–activity relationships for organic compounds. It was developed by Robert W. Taft in 1952 as a modification to the Hammett equation. While the Hammett equation accounts for how field, inductive, and resonance effects influence reaction rates, the Taft equation also describes the steric effects of a substituent. The Taft equation is written as:

Mukaiyama Taxol total synthesis

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Methanesulfonic acid Chemical compound

Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids. Salts and esters of methanesulfonic acid are known as mesylates (or methanesulfonates, as in ethyl methanesulfonate). It is hygroscopic in its concentrated form. Methanesulfonic acid can dissolve a wide range of metal salts, many of them in significantly higher concentrations than in hydrochloric or sulfuric acid.

The Schöllkopf method or Schöllkopf Bis-Lactim Amino Acid Synthesis is a method in organic chemistry for the asymmetric synthesis of chiral amino acids. The method was established in 1981 by Ulrich Schöllkopf. In it glycine is a substrate, valine a chiral auxiliary and the reaction taking place an alkylation.

References

  1. Olah, George A.; Narang, Subhash C.; Gupta, B. G. Balaram; Malhotra, Ripudaman (1979). "Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ Iodotrimethylsilane Reagent". J. Org. Chem. 44: 1247–1251. doi:10.1021/jo01322a012.
  2. "MSDS Methyl trimethylacetate".