Isopropyl iodide → 2-Isopropoxy-3-methylbenzaldehyde

HRID 2074412Notes

Reaction equation

HRID 2074412 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[C:3]=1[OH:10].[CH:11](I)([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][C:2]1[C:3]([O:10][CH:11]([CH3:13])[CH3:12])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 498745212-Isopropoxy-3-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Stir a mixture of 3-methylsalicylaldehyde (100 g, 0.73 mol), isopropyl iodide (187 g, 1.1 mol) and K2CO3 (141 g, 1.0 mol) in DMF (400 mL) for 20 hr at room temperature. TLC shows partial reaction; thus, add more isopropyl iodide (43 g, 0.25 mol) and heat the reaction to 45° C. with stirring for an additional 10 hr. Dilute the reaction mixture with H2O (1 L) and extract the resulting mixture with EtOAc. Wash the organic layer with 0.25 M. aqueous NaOH and then with H2O. Dry over MgSO4 and evaporate the solvent to give 3-methyl-2-isopropoxybenzaldehyde, 122 g (94%); 1H-NMR (CDCl3) δ 7.7-7.1 (m, 3H), 4.2 (m, 1H), 2.3 (s, 3H), 1.4 (d. 6H).

Workup

  1. customreaction
  2. temperatureheat
  3. customthe reaction to 45° C.
  4. stirringwith stirring for an additional 10 hr
  5. extractionextract the resulting mixture with EtOAc
  6. washWash the organic layer with 0.25 M
  7. dry with materialDry over MgSO4
  8. customevaporate the solvent

Sources & evidence

ORD record
ord-d64e119dc8e941c98d55bc034e55fc4a
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

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