Hydrochloric Acid → HCID 13090971, compound

HRID 2163403Notes

Reaction equation

HRID 2163403 reaction equation
[Na].[C:2]([C:5]1[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][C:6]=1[O:7][CH2:8][CH:9]([OH:22])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=1[C:19](=[O:21])[CH3:20])(=[O:4])[CH3:3].[C:28](OCC)(=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl>O.C(Cl)(Cl)Cl.C(O)C>[C:19]([C:13]1[C:14]([OH:18])=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH2:10][CH:9]([OH:22])[CH2:8][O:7][C:6]1[C:5]2[C:2](=[O:4])[CH:3]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[O:27][C:26]=2[CH:25]=[CH:24][CH:23]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 85303Acetophenone, 2',2'''-(2-hydroxytrimethylenedioxy)bis(6-hydroxy-HCID 5360545Sodium

Product 1

HCID 13090971HCID 13090971, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 69.0 parts of sodium in 1000 parts of ethanol was added to a mixture of 360.3 parts of 1,3-bis-(2-acetyl-3-hydroxyphenoxy)propan-2-ol, 146.1 parts of diethyl oxalate and 250 parts of ethanol. The reaction mixture was refluxed for five hours, then poured into a stirred mixture of 700 parts of chloroform, 3,000 parts of water and 285 parts of concentrated hydrochloric acid. The solid obtained was removed by filtration, the chloroform phase of the filtrate separated and the aqueous phase extracted with chloroform. The combined chloroform extracts were washed with water and concentrated to give a solid which was removed by filtration. Evaporation of the chloroform from the filtrate gave a residue which, after fractional crystallization from ethanol, gave 36.0 parts of slightly impure ethyl 5-(3-[2-acetyl-3-hydroxyphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylate, m.pt. 145°-148°.

Workup

  1. temperatureThe reaction mixture was refluxed for five hours
  2. customThe solid obtained
  3. customwas removed by filtration
  4. customthe chloroform phase of the filtrate separated
  5. extractionthe aqueous phase extracted with chloroform
  6. washThe combined chloroform extracts were washed with water
  7. concentrationconcentrated
  8. customto give a solid which
  9. customwas removed by filtration
  10. customEvaporation of the chloroform from the filtrate
  11. customgave a residue which
  12. customafter fractional crystallization from ethanol

Sources & evidence

ORD record
ord-8ad5e0b04df04feea61959230fc434f8
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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