Catechol → 2-(2,5-Dimethylphenylmethoxy)phenol

HRID 1284594Notes

Reaction equation

HRID 1284594 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH2:4]Cl.[C:11]1([C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[OH:14])[OH:12].[OH-].[K+]>C(O)C>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH2:4][O:12][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[OH:14]

Participants

5

Reactant 3

HCID 289CatecholHCID 14797Potassium HydroxideHCID 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-

Product 1

HCID 202522402-(2,5-Dimethylphenylmethoxy)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

For the synthesis of V, 15.00 g of 2,5-dimethylbenzyl chloride are added to 10.68 g of catechol dissolved in 10 ml of absolute ethanol under nitrogen. KOH, 5.44 g dissolved in 50 ml of ethanol, is added dropwise over 30 minutes with stirring. The solution is then refluxed under nitrogen for 2 hours. The solution is filtered to remove KCl. The solution is cooled over night and filtered to remove di-substituted product. Ethanol is removed by rotary evaporation, and the oil is dissolved in 50 ml of chloroform. The pH is adjusted to neutrality with HCl and extracted three times with equal volumes of water to remove unreacted catechol and salts. Chloroform is removed by rotary evaporation. The oil is vacuum-distilled at 8 mm Hg and the fraction containing V is collected.

Workup

  1. additionis added dropwise over 30 minutes
  2. temperatureThe solution is then refluxed under nitrogen for 2 hours
  3. filtrationThe solution is filtered
  4. customto remove KCl
  5. temperatureThe solution is cooled over night
  6. filtrationfiltered
  7. customto remove di-substituted product
  8. customEthanol is removed by rotary evaporation
  9. dissolutionthe oil is dissolved in 50 ml of chloroform
  10. extractionextracted three times with equal volumes of water
  11. customto remove unreacted catechol and salts
  12. customChloroform is removed by rotary evaporation
  13. distillationThe oil is vacuum-distilled at 8 mm Hg
  14. additionthe fraction containing V
  15. customis collected

Sources & evidence

ORD record
ord-d4ae03c4495744d2ba28382c416f5796
Source dataset
uspto-grants-1986_01
Patent number
US04563526

Reaction notes

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