Dimethylformamide → 2-(Propan-2-yloxy)benzaldehyde

HRID 870492Notes

Reaction equation

HRID 870492 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>[CH3:12][CH:11]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 6998SalicylaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 2500782-(Propan-2-yloxy)benzaldehydeYield 103.3%

Procedure

Into a 1000-mL 3-necked round-bottom flask was placed 2-hydroxybenzaldehyde (36 g, 294.79 mmol, 1.00 equiv), 2-iodopropane (100 g, 588.26 mmol, 2.00 equiv), potassium carbonate (122 g, 882.71 mmol, 2.99 equiv) and N,N-dimethylformamide (500 g, 6.84 mol, 23.21 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 1000 mL of water. The resulting solution was extracted with 3×500 mL of ethyl acetate and the organic layers combined, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 50 g (crude) of 2-(propan-2-yloxy)benzaldehyde as a yellow oil.

Workup

  1. customInto a 1000-mL 3-necked round-bottom flask was placed
  2. customThe reaction was then quenched by the addition of 1000 mL of water
  3. extractionThe resulting solution was extracted with 3×500 mL of ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4c36ea38a67946318a884aa183ca44fc
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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