2-(2-Chloro-5-(hydroxymethyl)phenyl)ethanol → 4-Chloro-3-(2-hydroxyethyl)benzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[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[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[CH2:10][CH2:11][OH:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Manganese (IV) dioxide (1.00 g) was added to a solution of 2-(2-chloro-5-(hydroxymethyl)phenyl)ethanol (example 75, step b) (0.205 g) in DCM (10 mL), and the resulting suspension was stirred at room temperature overnight. The mixture was then filtered through Celite, washing the filter pad well with DCM. The filtrate and washings were concentrated in vacuo to afford the subtitled compound as a colourless oil. Yield 0.159 g.
Workup
- filtrationThe mixture was then filtered through Celite
- washwashing the filter pad well with DCM
- concentrationThe filtrate and washings were concentrated in vacuo
Sources & evidence
- ORD record
- ord-8cfe514d2fe847adb7895e128a2ac64e
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629271B2
Reaction notes
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