2-[4-(Hydroxymethyl)phenyl]propan-2-ol → 4-(2-Hydroxypropan-2-yl)benzaldehyde
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1>C(OCC)(=O)C.ClCCl.O=[Mn]=O>[OH:12][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1)([CH3:11])[CH3:10]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
2-[4-(Hydroxymethyl)phenyl]propan-2-ol (1.0 g, 6 mmol) was dissolved in the mixture of ethyl acetate (10 mL) and dichloromethane (5 mL). To the solution, MnO2 (2.6 g, 30 mmol) was added, and the mixture was stirred overnight at room temperature. The solid was filtered off and washed with ethyl acetate. The combined organic phases were concentrated to afford the title compound. 1H NMR (400 MHz CDCl3): δ 10.00 (s, 1H), 7.80 (d, 2H), 7.60 (d, 2H), 1.60 (s, 6H).
Workup
- filtrationThe solid was filtered off
- washwashed with ethyl acetate
- concentrationThe combined organic phases were concentrated
Sources & evidence
- ORD record
- ord-656c0edb794d41698126c70cd4528d6a
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278335B2
Reaction notes
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