4-(Hydroxymethyl)phenylacetic acid → 2-(4-formylphenyl)acetic Acid
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[O:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To [4-(hydroxymethyl)phenyl]acetic acid (3 g, 18 mmol) in CHCl3 (50 mL) under N2 was added manganese dioxide (7.7 g, 90 mmol) and the reaction mixture was stirred at 50° C. for 18 h. The crude was filtered through a pad of celite, washed with DCM (50 mL) and concentrated under reduced pressure to give the desired product (1.76 g, 59%). 1H NMR (300 MHz, d6-DMSO) δ: 12.49 (1H, br s), 9.99 (1H, s), 7.89-7.84 (2H, m), 7.50 (2H, d, J=7.9 Hz), 3.72 (2H, s).
Workup
- filtrationThe crude was filtered through a pad of celite
- washwashed with DCM (50 mL)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4bcd1a5ba7974fd19b425ce2ea8132b3
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273003B2
Reaction notes
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