Novel rearrangement of 1,3-glycols was written by Crowdle, James H.;Knipper, Joseph E.;Schmidt, Jerome E.;Conley, Robert T.. And the article was included in Journal of Organic Chemistry in 1960.Quality Control of 2-Butyl-2-ethylpropane-1,3-diol The following contents are mentioned in the article:
The glycols, RR’C(CH2OH)2 (I, R = Me, Et, Et, R’ = Et, Et, Bu) (II, III, IV) with strong base in the presence of Na2SO3, NaAsO2, or Na2H3PO3 yielded approx. 50% mono alcs., RR’CMeCH2OH (V), also given by rearrangement of the corresponding cyclic sulfites, RR’C.CH2.O.SO.O.CH2 (VI) by strong base alone. H2O (1 mole), 3 moles NaOH, and 1.0 mole Na2SO3 treated slowly at 130-40° with 1.0 mole I, the mixture slowly cooled, and diluted with H2O gave 46-49% V. Similar treatment of VI with omission of Na2SO3 gave similar yields of the same products. The rearrangement was presumed to be an interesting 1-3 hydride shift to an aldehyde, with subsequent Cannizzaro reaction in the strongly basic medium. It was assumed that I formed only monosulfite and that the consequent steric compression of the substituents on the α-C atom facilitated the rearrangement to the aldehyde. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Quality Control of 2-Butyl-2-ethylpropane-1,3-diol).
2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Quality Control of 2-Butyl-2-ethylpropane-1,3-diol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts