4-Hydroxybenzaldehyde → 4-(2-Phenoxyethoxy)benzaldehyde

HRID 1739404Notes

Reaction equation

HRID 1739404 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[O:12]([CH2:19][CH2:20]CS([O-])(=O)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[O:12]([CH2:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 21841067HCID 21841067, compound

Product 1

HCID 134832164-(2-Phenoxyethoxy)benzaldehydeYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.19 g of 4-hydroxybenzaldehyde were dissolved in 30 ml of DMF, and 0.41 g of 60% NaH were further added to the resultant solution while cooling it with ice. The solution was then stirred for 1 hour after elevating the temperature of the solution up to room temperature. The solution was again cooled with ice, then added with 2.0 g of 2-phenoxyethyl-methane sulfonate, and stirred for 1 hour at room temperature and subsequently for a night at 50-60° C. The solution reacted was poured into ice-water and extracted with ethyl acetate, then the organic layer resulted was dried with anhydrous magnesium sulfate. The solvent used was then removed by distillation under reduced pressure, and the residue obtained was washed with a mixture of ether and hexane, thereby affording 1.45 g of 4-(2-phenoxyethyloxy)benzaldehyde.

Workup

  1. temperaturewhile cooling it with ice
  2. customup to room temperature
  3. temperatureThe solution was again cooled with ice
  4. stirringstirred for 1 hour at room temperature and subsequently for a night at 50-60° C
  5. customThe solution reacted
  6. extractionextracted with ethyl acetate
  7. customthe organic layer resulted
  8. dry with materialwas dried with anhydrous magnesium sulfate
  9. customThe solvent used was then removed by distillation under reduced pressure
  10. customthe residue obtained
  11. washwas washed with a mixture of ether and hexane

Sources & evidence

ORD record
ord-2070c0609afe47438e3a39baf707cd68
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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