Catechol → HCID 13588513, compound

HRID 1284593Notes

Reaction equation

HRID 1284593 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13])[OH:11].[OH-].[K+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:11][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[OH:13]

Participants

5

Reactant 3

HCID 289CatecholHCID 6992o-Xylyl bromideHCID 14797Potassium Hydroxide

Product 1

HCID 13588513HCID 13588513, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

For the synthesis of I, 10.0 g of a-bromo-o-xylene were added to 5.95 g of catechol dissolved in 10 ml of absolute ethanol under nitrogen. KOH, 3.3 g dissolved in 50 ml of ethanol, was added dropwise over 30 min with stirring. The solution was then refluxed under nitrogen for 2 hours. The solution was filtered to remove KBr. The solution was cooled over night and filtered to remove di-substituted product. Ethanol was removed by rotary evaporation, and the oil was dissolved in 50 ml of chloroform. The pH was adjusted to neutrality with HCl and extracted three times with equal volumes of water, to remove unreacted catechol and salts. Chloroform was removed by rotary evaporation and the oil was vacuum-distilled at 8 mm Hg. Approximately 4 g of compound I were collected in the distillate that came over at 180° C. The structure was confirmed by NMR and mass spectrum data.

Workup

  1. additionwas added dropwise over 30 min
  2. temperatureThe solution was then refluxed under nitrogen for 2 hours
  3. filtrationThe solution was filtered
  4. customto remove KBr
  5. temperatureThe solution was cooled over night
  6. filtrationfiltered
  7. customto remove di-substituted product
  8. customEthanol was removed by rotary evaporation
  9. dissolutionthe oil was dissolved in 50 ml of chloroform
  10. extractionextracted three times with equal volumes of water
  11. customto remove unreacted catechol and salts
  12. customChloroform was removed by rotary evaporation
  13. distillationthe oil was vacuum-distilled at 8 mm Hg
  14. distillationApproximately 4 g of compound I were collected in the distillate that
  15. customcame over at 180° C

Sources & evidence

ORD record
ord-f95910fad339455fa7f374c96511dc35
Source dataset
uspto-grants-1986_01
Patent number
US04563526

Reaction notes

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