(3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-5-bromophenyl)methanol → 3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-5-bromobenzaldehyde
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:22][OH:23])[CH:18]=[C:19]([Br:21])[CH:20]=1.[O-2].[Mg+4].[O-2]>O1CCOCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([Br:21])[CH:20]=1)[CH:22]=[O:23]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of (3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromophenyl)methanol (1.69 g, 4.36 mmol) in 1,4-dioxane (25 mL), was added magnesium (IV) oxide (1.90 g, 21.9 mmol). The reaction mixture was heated to 100° C. for 16 hours. The suspension was filtered, washed with ethyl acetate, and the filtrate was concentrated under reduced pressure to afford the title compound (1.25 g, 74%).