Pyridine → 1,4-Bis(benzoyloxymethyl)cyclohexane

Reaktionsgleichung

[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.N1C=C[CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[C:17]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][O:10][C:30](=[O:26])[C:29]2[CH:14]=[CH:13][CH:12]=[CH:27][CH:28]=2)[CH2:5][CH2:4]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

Edukt 4

HCID 1049Pyridine

HCID 7412Benzoyl chloride

HCID 77351,4-Cyclohexanedimethanol

HCID 8028Tetrahydrofuran

Produkt 1

HCID 1182441,4-Bis(benzoyloxymethyl)cyclohexaneAusbeute 95 %

Versuchsvorschrift

To 0.03 mol 1,4-dihydroxymethylcyclohexane were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl 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 recrystallization from ethyl acetate and petroleum ether (2:1 v/v) to give 1,4-di(benzoyloxymethyl)cyclohexane as a white solid. The yield was 95%, and m.p. was 111-113° C.