Potassium Iodide → HCID 22114752, compound

HRID 1276039Notes

Reaction equation

HRID 1276039 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Br[CH2:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+:23].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+].C(OC(=O)C)(=O)C>CN(C)C=O.O.C(N(CC)CC)C>[OH:18][CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:3]=[C:4]([C:11]([O-:13])=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6]([O-:8])=[O:7].[K+:23].[K+:23]

Participants

10

Reactant 6

HCID 4875Potassium IodideHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 118814-Hydroxyphthalic acidHCID 123083-Bromo-1-propanolHCID 2855718-Crown-6

Product 1

HCID 22114752HCID 22114752, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Five point zero (5.0) grams of 4-hydroxyphthalic acid and 13 g of 3-bromo-1-propanol were allowed to react in dimethylformamide while refluxing with heating in the presence of 10 g of potassium carbonate, a catalytic amount of 18-crown-6 and a catalytic amount of potassium iodide. The reaction was pursued with thin layer chromatography (TLC), heating was stopped when the reaction product became homogeneous and the temperature was lowered to room temperature. The reaction mixture was acetylated by the addition of acetic anhydride and triethylamine. Water was added to the reaction solution thereby the reaction was stopped. This mixture was extracted with ethyl acetate and the organic layer was concentrated. A methanol solution containing potassium hydroxide was added thereto and refluxed with heating, thereby white solids were formed. The solids formed were filtered, washed with ethyl acetate, and then dried, thereby 1.7 g of dipotassium 4-(3-hydroxypropoxy)-phthalate was obtained.

Workup

  1. temperaturewhile refluxing
  2. temperatureheating
  3. customwas lowered to room temperature
  4. extractionThis mixture was extracted with ethyl acetate
  5. concentrationthe organic layer was concentrated
  6. additionA methanol solution containing potassium hydroxide
  7. additionwas added
  8. temperaturerefluxed
  9. temperaturewith heating
  10. customwhite solids were formed
  11. customThe solids formed
  12. filtrationwere filtered
  13. washwashed with ethyl acetate
  14. customdried

Sources & evidence

ORD record
ord-19981a0b8bd3442d9dcfe9e1f1520844
Source dataset
uspto-grants-2000_12
Patent number
US06165707

Reaction notes

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