(3-((1,3-Dioxolan-2-yl)methyl)phenyl)methanol → 3-((1,3-Dioxolan-2-yl)methyl)benzaldehyde
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=1>O1CCOCC1.[O-2].[Mn+4].[O-2]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[CH:13]=[O:14]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of (3-((1,3-dioxolan-2-yl)methyl)phenyl)methanol (prepared as in Example 22, Step 1 with 3-((1,3-dioxolan-2-yl)methyl)benzoic acid replacing 4-((1,3-dioxolan-2-yl)methyl)benzoic acid; 0.47 g, 2.42 mmol) in 1,4-dioxane (8 mL), manganese (IV) oxide (2.35 g) was added. The resulting suspension was heated at 100° C. for 16 hours. The reaction mixture was allowed to cool, and the suspension was filtered through a pad of celite. The celite pad was washed with ethyl acetate and the filtrate evaporated at reduced pressure to afford the title compound (0.352 g, 76%).
Workup
- temperatureto cool
- filtrationthe suspension was filtered through a pad of celite
- washThe celite pad was washed with ethyl acetate
- customthe filtrate evaporated at reduced pressure
Sources & evidence
- ORD record
- ord-aecf4b55f3aa4ca0812ef3901afc8ad0
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877774B2
Reaction notes
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