Diethyl Ether → 3-Hydroxy-5-(propan-2-yl)benzaldehyde
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CCOCC>C(Cl)Cl>[OH:12][C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=1)[CH:2]=[O:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of 3-(hydroxymethyl)-5-isopropylphenol in 10 mL of CH2Cl2 was added 1.23 g (5.69 mmol) of PCC. The mixture was stirred for 4.5 h, Et2O was added, and the mixture was stored in a refrigerator. The solvent was concentrated, and the crude product was purified by flash silica gel chromatography (15% EtOAc/hexanes) to provide 218 mg of 3-hydroxy-5-isopropylbenzaldehyde as a pale yellow solid.
Workup
- concentrationThe solvent was concentrated
- customthe crude product was purified by flash silica gel chromatography (15% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-97d954bfe6d1478ba7e14a40f1427b22
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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