Homovanillic Acid → HCID 22600136, compound

HRID 1383372Notes

Reaction equation

HRID 1383372 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[C:7]([OH:19])(=[O:18])[CH2:8][C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1.[CH:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1>CC#N>[CH2:26]([O:15][C:14]1[CH:16]=[CH:17][C:9]([CH2:8][C:7]([O:19][CH2:8][C:9]2[CH:17]=[CH:16][CH:14]=[CH:11][CH:10]=2)=[O:18])=[CH:10][C:11]=1[O:12][CH3:13])[C:23]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1738Homovanillic AcidHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 22600136HCID 22600136, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cs2CO3 (17.88 g; 54.9 mmol) was added to a solution of homovanillic acid (2.0 g; 11 mmol) in CH3CN, whereafter BnBr (4.3 g; 24.15 mmol) was added dropwise over 10 minutes. The mixture was refluxed overnight, filtered through Hyflo and concentrated. The resulting mixture was dissolved in EtOAc (100 mL), water (30 mL) was added, and the aqueous layer was separated. The organic phase was washed with citric acid solution (5%, 1×20 mL) and brine, dried (Na2SO4), and evaporated to yield 4.25 g (quant.) of the sub-title compound.

Workup

  1. additionwas added dropwise over 10 minutes
  2. temperatureThe mixture was refluxed overnight
  3. filtrationfiltered through Hyflo
  4. concentrationconcentrated
  5. dissolutionThe resulting mixture was dissolved in EtOAc (100 mL)
  6. additionwater (30 mL) was added
  7. customthe aqueous layer was separated
  8. washThe organic phase was washed with citric acid solution (5%, 1×20 mL) and brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-217157bc32d84536acd8e88d3f23e31f
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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