Water → 4-(4-Propylphenoxy)benzaldehyde

HRID 129793

Reaction equation

HRID 129793 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:8][CH3:9].F[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.O>CN(C)C(=O)C.C(Cl)Cl>[CH2:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 125804-PropylphenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 106337934-(4-Propylphenoxy)benzaldehydeYield 69.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

Anhydrous potassium carbonate (14.9 g, 0.12 mol) was added to a mixture of 4-propylphenol (13.6 g, 0.10 mol) and 4-fluorobenzaldehyde (12.4 g, 0.10 mol) in N,N-dimethylacetamide (100 mL) under argon. The heterogeneous mixture was brought to reflux, maintained at that temperature for 5 h, then cooled to RT. Water (100 mL) and CH2Cl2 (100 mL) were added, resulting in a tri-phase system. The bottom layer was removed; the middle layer was dried over MgSO4 ; and, the top layer was extracted with CH2Cl2 (100 mL) and dried over MgSO4. The dried layers were combined and concentrated in vacuo at 50° C. to give an orange oil. The crude product was purified by distillation to give title compound (16.6 g, 69%) as a colorless oil. bp 133°-50° C. (0.2 mm Hg)

Workup

  1. temperatureto reflux
  2. temperaturemaintained at that temperature for 5 h
  3. customresulting in a tri-phase system
  4. customThe bottom layer was removed
  5. dry with materialthe middle layer was dried over MgSO4
  6. extractionand, the top layer was extracted with CH2Cl2 (100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo at 50° C.
  9. customto give an orange oil
  10. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-75fec20ea6da4c0285122fd49d36a5ab
Source dataset
uspto-grants-1995_11
Patent number
US05470845

Linked notes

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