Isopropyl iodide → 4-(Benzyloxy)-2-isopropoxybenzaldehyde

HRID 445861Notes

Reaction equation

HRID 445861 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH:19]([CH3:21])[CH3:20])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 106357444-(Benzyloxy)-2-isopropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(benzyloxy)-2-hydroxybenzaldehyde (1 g, 4.38 mol), 2-iodopropane (1.2 eq.) and potassium carbonate (2.5 eq.) in acetone (40 mL) was refluxed overnight. The reaction was cooled to room temperature and filtered through a celite plug, and concentrated to dryness. The crude material was purified by flash column chromatography with ethyl acetate and hexanes to provide 4-(benzyloxy)-2-isopropoxybenzaldehyde (698).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered through a celite plug
  3. concentrationconcentrated to dryness
  4. customThe crude material was purified by flash column chromatography with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-50fbca80130f490b8c5a7159b66c1d20
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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