Water → 2-Propoxy-benzaldehyde

HRID 619139Notes

Reaction equation

HRID 619139 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].I[CH2:13][CH2:14][CH3:15].O>CN(C=O)C>[CH2:13]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 336431-Iodopropane

Product 1

HCID 2498072-Propoxy-benzaldehydeYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of salicylaldehyde (12.21 g, 0.1 mol) in DMF (65 ml) was cooled in an ice/water bath under argon and 60% sodium hydride in mineral oil (4.0 g, 0.1 mol) was added in several portions. The mixture was stirred for one hour and then iodopropane (16.99 g, 0.1 mol) was added at room temperature. The reaction mixture was stirred at room temperature overnight, poured into water (800 ml) and stirred. The mixture was extracted with chloroform (3×), the chloroform layer was concentrated in vacuo and the dark oil thus obtained was distilled under vacuum (92-94° C. at 1.15 mm Hg) to afford 12.68 g (77%) of 2-propoxybenzaldehyde.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. stirringstirred
  3. extractionThe mixture was extracted with chloroform (3×)
  4. concentrationthe chloroform layer was concentrated in vacuo
  5. customthe dark oil thus obtained
  6. distillationwas distilled under vacuum (92-94° C. at 1.15 mm Hg)

Sources & evidence

ORD record
ord-fa2a4b42ad0d43678abc5d964173bc47
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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