Hydrochloric Acid → HCID 20289615, compound

HRID 1414060Notes

Reaction equation

HRID 1414060 reaction equation
[Na+].[C:2]([C:5]1[CH:33]=[CH:32][C:8]([O:9][CH2:10][CH:11]([OH:31])[CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]3[C:18](=[O:25])[CH:19]=[C:20]([C:22]([O-:24])=[O:23])[O:21][C:16]=3[C:15]=2[CH2:28][CH2:29][CH3:30])=[C:7]([CH2:34][CH2:35][CH3:36])[C:6]=1[OH:37])(=[O:4])[CH3:3].[I-:38].[I-].[I-].[K+].[K+].[K+].S(=O)(O)[O-].[Na+].II.Cl>[OH-].[NH4+]>[C:2]([C:5]1[CH:33]=[C:32]([I:38])[C:8]([O:9][CH2:10][CH:11]([OH:31])[CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]3[C:18](=[O:25])[CH:19]=[C:20]([C:22]([OH:24])=[O:23])[O:21][C:16]=3[C:15]=2[CH2:28][CH2:29][CH3:30])=[C:7]([CH2:34][CH2:35][CH3:36])[C:6]=1[OH:37])(=[O:4])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 23618803HCID 23618803, compoundHCID 236620257-((3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxyl))-4-oxo-8-propyl-4H-chromene-2-carboxy late, sodium saltHCID 23665763Sodium Bisulfite

Product 1

HCID 20289615HCID 20289615, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

Dissolve 10.9 gm of 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylic acid sodium salt in 250 ml of 28% ammonium hydroxide solution. Cool the mixture in an ice-water bath. Add 285 ml of a 0.2 m aqueous potassium triiodide solution dropwise. Stir in the cold for 15 minutes. Add sodium bisulfite until iodine color is discharged. Acidify the mixture slowly with 20% aqueous hydrochloric acid. Separate the solids by filtration, wash with water and dry. Dissolve the solids in methanol and esterify with diazomethane in ether. Chromatograph on silica gel, eluting with 15% ethyl acetate in toluene (mp 137°-141° C.). Crystallize from toluene (mp 150°-153° C.). Reflux 2.1 gm of ester product in a mixture of 2.1 gm of sodium bicarbonate, 200 ml of denatured alcohol and 20 ml of water for 1 hour. Strip the mixture to dryness and triturate the residue in ethyl acetate. Separate the solids, dissolve in water and acidify with 10% aqueous hydrochloric acid. Separate the solids by filtration. (mp 179°-182° C.)

Workup

  1. temperatureCool the mixture in an ice-water bath
  2. customSeparate the solids
  3. filtrationby filtration
  4. washwash with water
  5. customdry
  6. dissolutionDissolve the solids in methanol
  7. washChromatograph on silica gel, eluting with 15% ethyl acetate in toluene (mp 137°-141° C.)
  8. customCrystallize from toluene (mp 150°-153° C.)
  9. temperatureReflux 2.1 gm of ester product
  10. additionin a mixture of 2.1 gm of sodium bicarbonate, 200 ml of denatured alcohol and 20 ml of water for 1 hour
  11. customStrip the mixture to dryness and triturate the residue in ethyl acetate
  12. customSeparate the solids
  13. dissolutiondissolve in water
  14. customSeparate the solids
  15. filtrationby filtration

Sources & evidence

ORD record
ord-17bcc1be1d6d4d0282342732ba8fa521
Source dataset
uspto-grants-1981_02
Patent number
US04252818

Reaction notes

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