Hydroquinone → p-(n-Tetradecyloxy)phenol

HRID 247926Notes

Reaction equation

HRID 247926 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CC(C)=O>[CH2:31]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 8208Myristyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 192879p-(n-Tetradecyloxy)phenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a room temperature mixture of 40 g of hydroquinone, 62.76 g potassium carbonate, 3.02 g potassium iodide and 700 ml acetone is added, dropwise, 113.5 ml of 1-bromotetradecane. The reaction is heated at reflux temperature for 20 hours, cooled, filtered and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane) to give 36.5 g of the desired product as colorless crystals.

Workup

  1. additionis added
  2. temperatureThe reaction is heated
  3. temperatureat reflux temperature for 20 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dd3b4dd3c2d54c55ae454711b26ac503
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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