Rondestvedt, Christian S. Jr.’s team published research in Journal of the American Chemical Society in 84 | CAS: 1193-11-9

Journal of the American Chemical Society published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Related Products of dioxole.

Rondestvedt, Christian S. Jr. published the artcileNew rearrangement. Catalytic isomerization of m- dioxanes to β-alkoxy aldehydes. II. Scope and limitations, Related Products of dioxole, the publication is Journal of the American Chemical Society (1962), 3307-19, database is CAplus.

cf. CA 55, 10311b. Rearrangement of m-dioxanes to β-alkoxy aldehydes is effected by pumice or certain forms of silica at 250550°. Yields and conversions are generally good. The m-dioxanes from simple aliphatic aldehydes and ketones rearrange cleanly at about 400° on pumice; silica is active at 250-350°, but yields are slightly lower. Formals (R1 = R2 = H) are much more sluggish than other acetals and ketals. An acrolein acetal (R1 = CH2:CH; R2 = H) is inert to pumice but is rearranged smoothly by silica. A benzal (R1 = Ph, R2 = H) is isomerized with astonishing facility, but ring substituents (p-Cl, p-MeO, m-O2N, p-Me2N) generally retard strongly the rearrangement. Even p-alkyl groups are slightly inhibitory. The aryl acetals on silica are converted in part also to the aromatic aldehyde and to the substituted toluene. An ether oxygen in the substituents R1-R4 retards rearrangement. If R3 = R4 = H, rearrangement occurs, but the product is cleaved to acrolein and an alc. Acetals with 5- and 7-membered rings do not undergo the rearrangement, but rather are cleaved. Diacetals are inert to hot pumice, but some of them are converted to diether-dialdehydes in fair yields by silica.

Journal of the American Chemical Society published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Related Products of dioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem