Carbon Tetrachloride → HCID 21163137, compound

HRID 1278267Notes

Reaction equation

HRID 1278267 reaction equation
[C:1]([C:4]1[CH:36]=[CH:35][C:7]([O:8][CH2:9][CH:10]([OH:34])[CH2:11][O:12][C:13]2[CH:30]=[CH:29][C:16]3[C:17](=[O:28])[CH:18]=[C:19](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])[O:20][C:15]=3[C:14]=2[CH2:31][CH2:32][CH3:33])=[C:6]([CH2:37][CH2:38][CH3:39])[C:5]=1[OH:40])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].C(Cl)(Cl)(Cl)Cl>C(O)C>[C:1]([C:4]1[CH:36]=[CH:35][C:7]([O:8][CH2:9][CH:10]([OH:34])[CH2:11][O:12][C:13]2[CH:30]=[CH:29][C:16]3[C:17](=[O:28])[CH:18]=[C:19](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])[O:20][C:15]=3[C:14]=2[CH2:31][CH2:32][CH3:33])=[C:6]([CH2:37][CH2:38][CH3:39])[C:5]=1[OH:40])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 516892Sodium BicarbonateHCID 86737893HCID 86737893, compound

Product 1

HCID 21163137HCID 21163137, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of trans-ethyl 3-[7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-2-hydroxypropyloxy]-4-oxo-8-n-propyl-4H-1-benzopyran-2-yl]acrylate (1.56 g) and sodium hydrogen carbonate (1.56 g) in aqueous ethanol was refluxed for 1 hour. Ethanol was removed by distillation and the residual aqueous solution cooled. Acidification afforded a gum which solidified on prolonged treatment with refluxing carbon tetrachloride. Crystallisation from acetone-carbon tetrachloride yielded trans-3[7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-2-hydroxypropyloxy]-4-oxo-8-n-propyl-4H-1-benzopyran-2-yl]acrylic acid (0.58 g) mp 101°-103° C.

Workup

  1. customEthanol was removed by distillation
  2. temperaturethe residual aqueous solution cooled
  3. customAcidification afforded a gum which
  4. customCrystallisation from acetone-carbon tetrachloride

Sources & evidence

ORD record
ord-b8cc216e11b049c4bedf2fe8133ebf1f
Source dataset
uspto-grants-1981_07
Patent number
US04281008

Reaction notes

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