Ethanol → HCID 20129995, compound

HRID 845708Notes

Reaction equation

HRID 845708 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1O)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-:14].[Na+].CC(CC)CCC[C:21]1[CH:22]=[C:23](S([O-])(=O)=O)[C:24]([CH3:27])=[CH:25][CH:26]=1.[CH2:34](O)[CH3:35]>O>[CH3:5][CH:4]([CH2:34][CH3:35])[CH2:3][CH2:2][CH2:1][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:14][CH2:27][C:24]2[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19363527HCID 19363527, compoundHCID 86742282HCID 86742282, compound

Product 1

HCID 20129995HCID 20129995, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of pentyloxyphenol (50 g, 0.25 mol) dissolved in ethanol (250 ml) was added a solution of NaOH (12 g, 0.30 mol) dissolved in water (12 ml), followed by dropwise adding to the mixture, (±)-p-(4-methylhexyl)toluenesulfonate (79 g, 0.27 mol), heating the resulting mixture under reflux for 10 hours, distilling off ethanol after completion of the reaction, extracting with toluene, washing the resulting organic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, distilling off the solvent to obtain an oily (±)-p-benzyloxyphenyl 4-methylhexyl ether (79 g) and subjecting this p-benzyloxyphenyl 4-methylhexyl ether to hydrogenolysis with 5% paradium-carbon to obtain the objective (±)-p-(4-methylhexyloxy)phenol (VII) (37 g).

Workup

  1. temperatureheating the resulting mixture
  2. temperatureunder reflux for 10 hours
  3. distillationdistilling off ethanol
  4. customafter completion of the reaction
  5. extractionextracting with toluene
  6. washwashing the resulting organic layer with 6N-hydrochloric acid
  7. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-0c4b8cb73193494d9a5ad54cb52ac634
Source dataset
uspto-grants-1988_07
Patent number
US04759869

Reaction notes

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