Kojic Acid → HCID 59299997, compound

HRID 2236556Notes

Reaction equation

HRID 2236556 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CC(=O)CC>[OH:10][CH2:9][C:2]1[O:3][CH:4]=[C:5]([O:8][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:6](=[O:7])[CH:1]=1

Participants

6

Reactant 4

HCID 3840Kojic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

HCID 59299997HCID 59299997, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of kojic acid (28.4 g, 0.20 mole), 300 mL of 2-butanone, potassium carbonate powder (27.6 g, 0.20 mole), potassium iodide (1.66 g, 0.01 mole), and 1-(2-chloro-ethyl)-pyrrolidine (26.7 g, 0.20 mole) is stirred at a gentle reflux overnight. The reaction mixture is cooled, filtered, washed with acetone and the filtrate evaporated. Water is added and extracted with chloroform (3×100 mL) and ethyl acetate (6×100 mL). The combined organics were dried with sodium sulfate and passed through a pad of magnesol and silica gel eluting with ethyl acetate. The eluate is evaporated in vacuo and crystallized with hexane/ethyl acetate (2/1) to give an off-white solid, 3.05 g, (6%); MS (ES+): m/z 240.3 (M+H).

Workup

  1. temperaturea gentle reflux overnight
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. washwashed with acetone
  5. customthe filtrate evaporated
  6. additionWater is added
  7. extractionextracted with chloroform (3×100 mL) and ethyl acetate (6×100 mL)
  8. dry with materialThe combined organics were dried with sodium sulfate
  9. customThe eluate is evaporated in vacuo
  10. customcrystallized with hexane/ethyl acetate (2/1)
  11. customto give an off-white solid, 3.05 g, (6%)

Sources & evidence

ORD record
ord-ed9c9e3a394040bd9d08d9c4782cb6dc
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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