Process for producing tetrahydropyran-4-ol, intermediate...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C549S423000

Reexamination Certificate

active

10516756

ABSTRACT:
The present invention relates to a process for preparing tetrahydropyran-4-ol which comprises the steps of (A) a cyclization step of preparing tetrahydropyranyl-4-formate represented by the formula (1):by reacting 3-buten-1-ol, a formaldehyde compound and formic acid, and(B) then, a solvolysis step of subjecting the tetrahydropyranyl-4-formate to solvolysis to obtain tetrahydropyran-4-ol represented by the formula (2):and an intermediate and a process for preparing the same.

REFERENCES:
patent: WO 01/42232 (2001-06-01), None
Gelin, Rene et al, Etude de la reaction de Prins entre des alcools β-ethyleniques et le formaldehyde, Comptes Rendus des Seances d l' Academie des Sciences, Serie C: Sciences Chimiques, 1972, vol. 275, No. 17, pp. 957-959.
Hanschke, E. et al, Zur Kenntnis der Prins schen Reaction, III. Mitteil.: Uber die Reaction von Allylcarbinol mit Aldehyden und Ketonen, Chem Ber., 1955, vol. 88, pp. 1053-1061.
Gerin, Rene et al, Etude de la reaction de Prins entre des alcohols β-ethyleniques et des aldehydes, Synthese de tetrahydropyrannols-4, Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 275, pp. 254-256.
Nishiura, Kazuo et al, The Reaction of Olefins with Chloroalkoxy-alkanes and Formic Acid in Ether, Bull. Chem. Soc. Jpn., 1980, vol. 53, pp. 1376-1380.
Fukui, Kenishi et al, Reaction of Propylene with Formaldehyde, Bull, Japan, Petrol. Inst., 1961, vol. 3, pp. 27-32.

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