Hydrochloric Acid → HCID 22753579, compound

HRID 2163406Notes

Reaction equation

HRID 2163406 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:34]([OH:35])=[CH:33][CH:32]=[CH:31][C:8]=1[O:9][CH2:10][CH:11]([OH:30])[CH2:12][O:13][C:14]1[C:19]2[C:20](=[O:29])[CH:21]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:6].C(O)C.Cl.O>C(Cl)(Cl)Cl>[O:6]=[C:5]1[C:7]2[C:8]([O:9][CH2:10][CH:11]([OH:30])[CH2:12][O:13][C:14]3[C:19]4[C:20](=[O:29])[CH:21]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[O:23][C:18]=4[CH:17]=[CH:16][CH:15]=3)=[CH:31][CH:32]=[CH:33][C:34]=2[O:35][CH:3]=[CH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 54243444HCID 54243444, compound

Product 1

HCID 22753579HCID 22753579, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.200 parts of ethyl 5-(3-[2-{3-dimethylaminoacryloyl}-3-hydroxyphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylate were refluxed for 16 hours in 15.8 parts of ethanol containing 1 part of concentrated hydrochloric acid. The solution was poured into a stirred mixture of 10 parts of water and 73 parts of chloroform and the organic extract separated, and washed with 5% sodium bicarbonate solution and water. Evaporation of the chloroform gave a residue which was chromatographed on silica gel, eluting with 1:1 chloroform/ethyl acetate. The product obtained from chromatography was crystallised from ethanol to give 0.027 parts of ethyl 5-(3-[4-oxo-4H-1-benzopyran-5-yloxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylate, m.pt. 154°-158°.

Workup

  1. extractionthe organic extract
  2. customseparated
  3. washwashed with 5% sodium bicarbonate solution and water
  4. customEvaporation of the chloroform
  5. customgave a residue which
  6. customwas chromatographed on silica gel
  7. washeluting with 1:1 chloroform/ethyl acetate
  8. customThe product obtained from chromatography
  9. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-2936b72faf154937b69f245312d03428
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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