Hydrochloric Acid → HCID 19438325, compound

HRID 1534416Notes

Reaction equation

HRID 1534416 reaction equation
O[C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:14][CH2:15][CH2:16]Br.[OH-:18].[K+].Cl>O>[O:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:9][C:10]([OH:12])=[O:11])=[CH:3][C:2]=2[CH2:16][CH2:15][CH2:14][O:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 547DopacHCID 80011,3-DibromopropaneHCID 14797Potassium Hydroxide

Product 1

HCID 19438325HCID 19438325, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-dihydroxyphenylacetic acid (5.0 g), 1,3-dibromopropane (7.2 g) and potassium hydroxide (7.3 g) in water (25 ml) was heated under reflux for 17 hours, acidified to pH 1 with 2M hydrochloric acid and extracted several times into methylene chloride. The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (75 g) using methylene chloride plus 0-2% acetic acid as the eluant. Appropriate fractions were combined and evaporated and the residue was taken up in methylene chloride and extracted into 5% aqueous sodium carbonate solution. The basic extract was washed with methylene chloride, acidified to pH 1 with 5M hydrochloric acid and extracted into methylene chloride. The organic extract was dried over magnesium sulphate and evaporated to give the title compound as a colourless solid (1.4 g, 23%), m.p. 99°-101°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours
  3. extractionextracted several times into methylene chloride
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (75 g)
  7. customevaporated
  8. extractionextracted into 5% aqueous sodium carbonate solution
  9. extractionThe basic extract
  10. washwas washed with methylene chloride
  11. extractionextracted into methylene chloride
  12. extractionThe organic extract
  13. dry with materialwas dried over magnesium sulphate
  14. customevaporated

Sources & evidence

ORD record
ord-af84a1fc560b47ce83d2ffcf47f09fbe
Source dataset
uspto-grants-1992_02
Patent number
US05089505

Reaction notes

Loading…