4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

HRID 53099Notes

Reaction equation

HRID 53099 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[O:2].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 90358p-(Octyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution containing 3.053 g (25 mmol) of 4-formylphenol, 6.48 ml (3705 mmol) of 1-bromooctane and 6.9 mg (50 mmol) of potassium carbonate in 100 ml of acetone was refluxed overnight. When the reaction was substantially complete, as indicated by thin layer chromatagraphy (TLC), the reaction was quenched by the addition of 100 ml of water. The desired compound was extracted from the reaction mixture using two 100 ml portions of diethyl ether. The resultant solution was dried over magnesium sulfate, filtered and then concentrated in vacuo to provide a liquid which was purified using HPLC (eluent of 10 ethyl acetate in hexane) to provide the desired compound.

Workup

  1. temperaturewas refluxed overnight
  2. customthe reaction was quenched by the addition of 100 ml of water
  3. extractionThe desired compound was extracted from the reaction mixture
  4. dry with materialThe resultant solution was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a liquid which
  8. customwas purified

Sources & evidence

ORD record
ord-bbd2d797dc224e55945d075f0efd3385
Source dataset
uspto-grants-1997_04
Patent number
US05618787

Reaction notes

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