CA2236382A1 - Process for the production of 2h-1-benzopyrans - Google Patents

Process for the production of 2h-1-benzopyrans

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Publication number
CA2236382A1
CA2236382A1 CA002236382A CA2236382A CA2236382A1 CA 2236382 A1 CA2236382 A1 CA 2236382A1 CA 002236382 A CA002236382 A CA 002236382A CA 2236382 A CA2236382 A CA 2236382A CA 2236382 A1 CA2236382 A1 CA 2236382A1
Authority
CA
Canada
Prior art keywords
group
alkyl group
general formula
hydrogen
mentioned meaning
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002236382A
Other languages
French (fr)
Other versions
CA2236382C (en
Inventor
Pierre Bossard
Frances Finney
Michael Gottsponer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SmithKline Beecham Ltd
Original Assignee
Smithkline Beecham P.L.C.
Pierre Bossard
Frances Finney
Michael Gottsponer
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Smithkline Beecham P.L.C., Pierre Bossard, Frances Finney, Michael Gottsponer filed Critical Smithkline Beecham P.L.C.
Priority claimed from PCT/EP1997/004569 external-priority patent/WO1998006713A1/en
Publication of CA2236382A1 publication Critical patent/CA2236382A1/en
Application granted granted Critical
Publication of CA2236382C publication Critical patent/CA2236382C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)

Abstract

A process for the production of 2H-1-benzopyrans with general formula (I) where R1 is hydrogen, a (C1-C4) alkyl group, R2 is hydrogen, a (C1-C6) alkyl group and R3 is hydrogen, a (C1-C4) alkyl group, a (C1-C4) haloalkyl group, a (C2-C4) alkenyl group, a (C1-C4) alkoxycarbonyl group, a (C1-C4) alkoxymethyl group, a (C1-C4) alkanoyl group, a (C1-C4) alkoxy group, a (C1-C4) alkylsulphonyl group, halogen, amino alkylamino, dialkylamino nitril, nitro or hydroxy, is characterised in that in a first stage an aliphatic aldehyde with general formula (II) where R1 and R2 have the above-mentioned meaning, is converted with an aliphatic alcohol with the formula R4OH
or HOR4OH, where R4 is a (C1-C4) alkyl group or a (C2-C4) alkyldiyl group, in the presence of a dehydrating compound with the formula HC(OR5)3, where R5 is a (C1-C4) alkyl group, and an aluminium oxide/silicium oxide catalyst into an aliphatic acetal with general formula (III) where R1 and R2 have the above-mentioned meaning and R4 as stated above is a (C1-C4) alkyl group or the two R4 together are a cyclical (C2-C4) alkyldiyl group, and this is then condensed in a second stage with a phenol with general formula (IV) where R3 has the above-mentioned meaning, in the presence of a base in an inert organic solvent, to the end product with general formula (I).
CA002236382A 1996-08-13 1997-08-13 Process for the production of 2h-1-benzopyrans Expired - Lifetime CA2236382C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH198496 1996-08-13
CH1984/96 1996-08-13
PCT/EP1997/004569 WO1998006713A1 (en) 1996-08-13 1997-08-13 Process for the production of 2h-1-benzopyrans

Publications (2)

Publication Number Publication Date
CA2236382A1 true CA2236382A1 (en) 1998-02-19
CA2236382C CA2236382C (en) 2006-02-07

Family

ID=35892210

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002236382A Expired - Lifetime CA2236382C (en) 1996-08-13 1997-08-13 Process for the production of 2h-1-benzopyrans

Country Status (1)

Country Link
CA (1) CA2236382C (en)

Also Published As

Publication number Publication date
CA2236382C (en) 2006-02-07

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Effective date: 20170814