Reaktion #445534

Reaktionsgleichung

water

4hydroxycyclohexanone

p-toluenesulfonic acid monohydrate

→

sub-titled intermediate

8-Hydroxy-1,4-dioxaspiro[4.5]decane

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethree-necked, round-bottomed flask equipped with a Dean-Stark trap
2. 2
   Sonstigehad been removed
3. 3
   SonstigeSolvent was removed by distillation
4. 4
   workup.DISTILLATIONthe residue was fractionally distilled at 85°-88.5° C. (0.08 mm Hg.)

Vorschrift

A mixture of 4hydroxycyclohexanone (228 g, 2.0 mol) ethylene glycol (124 g, 2.0 mol) and p-toluenesulfonic acid monohydrate (0.89 g) in 2.0 l of benzene was stirred at reflux in a 3-l, three-necked, round-bottomed flask equipped with a Dean-Stark trap. The mixture was refluxed until the required amount of water had been removed. Solvent was removed by distillation and the residue was fractionally distilled at 85°-88.5° C. (0.08 mm Hg.) to give 247.8 g of the sub-titled intermediate. (78%), Lit bp 90°-95° C. (0.2 mm Hg.). (M. K. Batuev, et al., Ixvest. Akad. Nauk S.S.S.R., Otdel, Khim Nauk, 1960, 538-549.) IR, OH (3420), C--O (1105, 1035, 920); Mass Spectrum, m/e 158 (M+).

Quelle