Potassium Iodide → 4-[(9-Oxo-9H-thioxanthen-2-yl)oxy]butanoic acid

HRID 1649564Notes

Reaction equation

HRID 1649564 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.Cl[CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:21]([CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1)([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18474Ethyl 4-chlorobutyrateHCID 97945682-Hydroxy-9H-thioxanthen-9-one

Product 1

HCID 204791184-[(9-Oxo-9H-thioxanthen-2-yl)oxy]butanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-thioxanthone (4.56 g) was mixed with dimethylformamide (125 ml), ethyl 4-chlorobutyrate (6.02 g), potassium carbonate (2.80 g) and potassium iodide (0.50 g) and the mixture was stirred under reflux for four hours. The resulting mixture was poured carefully with stirring into cold distilled water. The yellow solid which precipitated, which is the ethyl ester of 2-(3-carboxypropoxy)thioxanthone, was collected by filtration and recrystallised from ethanol. The ethyl ester of 2-(3-carboxy-propoxy)thioxanthone (4.2 g) was dissolved in triethanolamine (50 ml) and a solution of potassium hydroxide (5.0 g) in distilled water (5 ml) and ethanol (20 ml) was slowly added with stirring. The resulting mixture was stirred under reflux for two hours, cooled, poured into a large excess of distilled water, and then acidified with hydrochloric acid. The resulting yellow precipitate was filtered off and recrystallised from ethanol to give 2-(3-carboxy-propoxy)thioxanthone.

Workup

  1. temperatureunder reflux for four hours
  2. additionThe resulting mixture was poured carefully
  3. stirringwith stirring
  4. distillationinto cold distilled water
  5. customThe yellow solid which precipitated
  6. filtrationwas collected by filtration
  7. customrecrystallised from ethanol
  8. dissolutionThe ethyl ester of 2-(3-carboxy-propoxy)thioxanthone (4.2 g) was dissolved in triethanolamine (50 ml)
  9. additiona solution of potassium hydroxide (5.0 g) in distilled water (5 ml) and ethanol (20 ml) was slowly added
  10. stirringwith stirring
  11. stirringThe resulting mixture was stirred
  12. temperatureunder reflux for two hours
  13. temperaturecooled
  14. additionpoured into a large excess of distilled water
  15. filtrationThe resulting yellow precipitate was filtered off
  16. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-27fc2265adad4ebfb069d2d44c9fa6df
Source dataset
uspto-grants-1983_11
Patent number
US04418138

Reaction notes

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