CA2236382A1 - Process for the production of 2h-1-benzopyrans - Google Patents
Process for the production of 2h-1-benzopyransInfo
- 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
Links
Landscapes
- 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).
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).
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) |
-
1997
- 1997-08-13 CA CA002236382A patent/CA2236382C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2236382C (en) | 2006-02-07 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20170814 |