4-Iodophenol → HCID 58773798, Verbindung

Reaktionsgleichung

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[I:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:15][CH:14]=1

Komponenten

Versuchsvorschrift

Ethyl 6-bromohexanoate (5.55 g, 25 mmol) in acetone (100 ml) was treated with 4-iodophenol (5.55 g, 25 mmol) and potassium carbonate (6.9 g 50 mmol). The stirred reaction was heated under reflux for 60 h. The reaction was then allowed to cool and the reaction concentrated in vacuum to a gum. The reaction was them partitioned between ethyl acetate (100 ml) and water (100 ml). The ethyl acetate layer was separated dried, over magnesium sulfate and concentrated in vacuo to give a colourless gum (8.71 g, 24.1 mmol, 96%), δH (CDCl3) 1.26 (3H, t, CO2CH2CH3), 1.46-1.81 (6H, m, 3,4,5-CH2), 2.33 (2H, t, 2-CH2), 3.91 (2H, t, 6-CH 2), 4.13 (2H, q, CO2CH2CH3), 6.66 (2H, dd, 2,6-ArH), 7.53 (2H, dd, 3,5-ArH), δH (CDCl3) 14.20, 24.60, 25.53, 28.75, 34.14, 60.20, 67.67, 82.44, 116.83,1 38.09, 158.84, and 173.52.