(4-Chloro-3-methoxyphenyl)methanol → 4-Chloro-3-methoxybenzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH3:11]>C1C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[O:10][CH3:11]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (4-chloro-3-methoxyphenyl)methan-1-ol (5.08 g, 29.4 mmol) in benzene (120 mL) was added MnO2 (5.65 g, 65 mmol). The reaction mixture was refluxed for 17 hr, chilled, and filtered through Celite, washing the cake with CH2Cl2 (300 mL). The filtrate was concentrated in vacuo to give 4-chloro-3-methoxybenzaldehyde (4.5 g, 89%).
Workup
- temperatureThe reaction mixture was refluxed for 17 hr
- temperaturechilled
- filtrationfiltered through Celite
- washwashing the cake with CH2Cl2 (300 mL)
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-f074e120e9b04d9f9e37f175fd9d00c9
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524721B2
Reaction notes
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