Diethyl Ether → 3-Hydroxy-5-(propan-2-yl)benzaldehyde

HRID 2071084Notes

Reaction equation

HRID 2071084 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

HCID 3283Diethyl EtherHCID 686702963-(Hydroxymethyl)-5-isopropylphenolHCID 178418287HCID 178418287, compound

Product 1

HCID 574477143-Hydroxy-5-(propan-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. concentrationThe solvent was concentrated
  2. 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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