4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

HRID 128778

Reaction equation

HRID 128778 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[CH2:13]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 81401-BromooctaneHCID 24758Sodium hydride

Product 1

HCID 90358p-(Octyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (4.2 g of 60% dispersion in oil) is added to a solution of 4-hydroxybenzaldehyde (12.2 g) in dimethylformamide. The mixture is stirred for 30 min, and 1-bromooctane (18 ml) is added. The reaction mixture is stirred at 90° for five hours, cooled, and the solvent removed in vacuo. The residue is shaken with water, and extracted with three portions of hexane. The hexane extracts are dried, concentrated, and distilled in vacuo to provide 20.3 g of 4-octyloxybenzaldehyde.

Workup

  1. stirringThe reaction mixture is stirred at 90° for five hours
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. stirringThe residue is shaken with water
  5. extractionextracted with three portions of hexane
  6. dry with materialThe hexane extracts are dried
  7. concentrationconcentrated
  8. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-9d34e36668c044eab835a9a616aded82
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Linked notes

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