Benzaldehyde → Benzylidene Dihexanoate

Reaktionsgleichung

[CH:1](=[O:8])[C:2]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(=O)(=O)(O)O.[C:29](Cl)(Cl)(Cl)Cl>>[C:9]([O:16][CH:17]([O:23][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:18]1[CH:29]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

Edukt 4

HCID 240Benzaldehyde

HCID 1118Sulfuric Acid

HCID 5943Carbon Tetrachloride

HCID 74918Hexanoic anhydride

Produkt 1

HCID 22116394Benzylidene Dihexanoate

Versuchsvorschrift

Benzaldehyde (26.3 g, 0.25 mol) and hexanoic acid anhydride (53.3 g, 0.25 mol) were dissolved in carbontetrachloride (200 ml) under N2 -atrnosphere. Catalytic amounts of sulfuric acid was added and the reaction mixture stirred at room temperature for 1 hr. The reaction mixture was evaporated over night, the residue dissolved in hexane and the solution filtered through a bed of silica. The filtrate was purified on a silica column, eluting with hexane. The evaporated eluate was a colourless oil and the yield was 14.0 g, 18% of the theoretical. 1H- and 13C NMR (CDCl3) d (ppm) rel. to TMS: 7.72 (s, 1H, CH(OC5H11)2), 7.58-7.39 (m, 5H, Ar-H), 2.37 (double t, 4 H, COCH2), 1.64 (m, 4H, COCH2CH2), 1.30 (m, 4H,CH2CH2CH3) and 0.88 (t, 6H, CH3); 171.524 (C=O), 135.688, 129.523, 128.466 and 126.547 (Ar), 89.398 (CH(OC5H11)2), 33.965, 31.030, 24.235 and 22.179 (CH2) and 13.777 (CH3).