Reaktionsgleichung
[CH3:1][CH:2]([OH:7])[CH2:3][CH:4]([OH:6])[CH3:5].N1C=CC=CC=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:23](Cl)[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[O:33]1CCCC1>>[C:23]([O:6][CH:4]([CH3:5])[CH2:3][CH:2]([O:7][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:1])(=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Komponenten
Versuchsvorschrift
To 0.03 mol 2,4-pentanediol were added 30 ml tetrahydrofuran and 0.04 mol pyridine, then added 0.03 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled. Then to the reaction were added 20 ml tetrahydrofuran and 0.05 mol pyridine, followed by 0.04 mol cinnamyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by column chromatography to give 2,4-pentanediol monobenzoate monocinnamate as a colorless liquid. The yield was 89%. 1HNMR: δ (ppm) 0.8-1.4(8H, m, CH3), 1.9-2.1(1H, m, CH), 5.1-5.3(2H, m, CH linked to ester radical), 6.2-8.0(12H, m, ArH and ═CH—)
Aufarbeitung
- temperatureThe reaction was heated
- temperaturerefluxing for 4 hours
- temperaturecooled
- stirringwith stirring
- temperatureThe reaction was heated
- temperaturerefluxing for 4 hours
- temperaturecooled
- additionadded 20 ml saturated saline
- extractionThe reaction mixture was extracted with ethyl acetate
- dry with materialthe extract was dried over anhydrous sodium sulfate
- filtrationfiltered
- customAfter removing solvent
- customthe crude was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-cb7a91e2125e4369bbec1f28d17a9e49
- Quelldatensatz
- uspto-grants-2008_06
- Patentnummer
- US07388061B2
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