Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([O:16]C)=[O:15].[CH3:18][O:19][C:20]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[CH:24][C:21]=1[CH:22]=O.C[O-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[CH:22][C:21]1[CH:24]=[CH:25][C:26]([O:30][CH3:31])=[C:27]([O:28][CH3:29])[C:20]=1[O:19][CH3:18])[C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=[O:15]Komponenten
Versuchsvorschrift
To a solution of methyl 5-methoxy-2-methyl-3-indenylacetate 8.7 g (0.037 mol) and 2,3,4-trimethoxybenzaldehyde, 7.99 g (1.1 equivalent) is added 16+ ml (2.0+ equivalents) of 25% methanolic sodium methoxide. The mixture is stirred at reflux under nitrogen for 2 hours. An equal volume of water is added dropwise and refluxing continues for 30 min. The solution is cooled, diluted with water and extracted with ether (3×). Residual ether is blown off with nitrogen, and then the aqueous solution is acidified with 50% glacial acetic acid. The precipitated product is collected and washed thoroughly with water. The crude product is crystallized to give 5-methoxy-2-methyl-1-(2,3,4-trimethoxybenzylidene)-3-indenyl acetic acid. (R and R1 =H, R2 =OCH3, R3 and R4 =H, R5, R6 and R7 =OCH3, R8 =CH3, R9 =H, R10 and R11 =double bond, m=0, n=0, M=OH)
Aufarbeitung
- temperatureat reflux under nitrogen for 2 hours
- temperaturerefluxing
- temperatureThe solution is cooled
- extractionextracted with ether (3×)
- customThe precipitated product is collected
- washwashed thoroughly with water
- customThe crude product is crystallized
Quellen und Nachweise
- ORD-Eintrag
- ord-676318bb322d465ea01df9cfd8f58359
- Quelldatensatz
- uspto-grants-2000_09
- Patentnummer
- US06121321
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