Isopropyl iodide → 3-Ethyl-4-isopropoxy-benzaldehyde

HRID 1066612Notes

Reaction equation

HRID 1066612 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH:18](I)([CH3:20])[CH3:19]>CN(C=O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:18]([CH3:20])[CH3:19])[CH:6]=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 220387133-Ethyl-4-hydroxybenzaldehyde

Product 1

HCID 220392013-Ethyl-4-isopropoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the 3-ethyl-4-hydroxy-benzaldehyde (7.8 g, 51.9 mmol) obtained in Example 179.1, K2CO3 (10.8 g, 78 mmol) and isopropyl iodide (7.86 ml, 78 mmol) was heated in DMF (65 ml) for 3 h. to 80° C. and subsequently stirred for 12 h. at room temperature. The mixture was poured into ice-cold 0.5M HCl and extracted with diethyl ether. The organic phase was washed with NaCl solution, dried, filtered and concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 4:1). 3-Ethyl-4-isopropoxy-benzaldehyde was obtained as an orange oil (6.12 g, 61%); MS: 192 ([M]+).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with NaCl solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (SiO2, hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-75b0b967b5354bd2a46ae4360ececb52
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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