2-(2-Chloro-3-(hydroxymethyl)phenyl)ethanol → 2-Chloro-3-(2-hydroxyethyl)benzaldehyde
Reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][OH:12]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]([CH2:10][CH2:11][OH:12])=[CH:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Manganese (IV) dioxide (1.599 g) was added to a solution of 2-(2-chloro-3-(hydroxymethyl)phenyl)ethanol (example 80, step c) (0.342 g) in DCM (20 mL), and the resulting suspension was stirred at room temperature overnight. The mixture was then concentrated onto silica and purified by flash chromatography on silica eluted with 25% ethyl acetate in isohexane to afford the subtitled compound as a white crystalline solid. Yield 0.223 g.
Workup
- concentrationThe mixture was then concentrated onto silica
- custompurified by flash chromatography on silica
- washeluted with 25% ethyl acetate in isohexane
Sources & evidence
- ORD record
- ord-4b96bf61c16d4c659ffce056338ae80a
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Reaction notes
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