Thionyl Chloride → 6,7-Bis(2,2,2-trichloroethoxycarbonyloxy)chromone-3-carbonyl chloride

HRID 67098Notes

Reaction equation

HRID 67098 reaction equation
[Cl:1][C:2]([Cl:32])([Cl:31])[CH2:3][O:4][C:5]([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])[O:14][CH:13]=[C:12]([C:27]([OH:29])=O)[C:11]2=[O:30])=[O:6].S(Cl)([Cl:35])=O>C1C=CC=CC=1>[Cl:1][C:2]([Cl:31])([Cl:32])[CH2:3][O:4][C:5]([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:24])[Cl:25])=[O:20])[O:14][CH:13]=[C:12]([C:27]([Cl:35])=[O:29])[C:11]2=[O:30])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 128006276,7-Bis(2,2,2-trichloroethoxycarbonyloxy)chromone-3-carboxylic acid

Product 1

HCID 128006286,7-Bis(2,2,2-trichloroethoxycarbonyloxy)chromone-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6,7-Bis(2,2,2-trichloroethoxycarbonyloxy)chromone-3-carboxylic acid (57.3 mg) was dissolved in benzene (10 ml). To the solution was added with stirring at room temperature thionyl chloride (0.5 ml). The mixture was refluxed with stirring for three hours, and the reaction solution was concentrated. To the concentrate was added n-hexane (5 ml) to cause crystallization of the reaction product. The resulting product was recovered by filtration and washed with n-hexan and dried. There were thus obtained 34.8 mg of the desired product (34.8 mg).

Workup

  1. additionTo the solution was added
  2. temperatureThe mixture was refluxed
  3. concentrationthe reaction solution was concentrated
  4. additionTo the concentrate was added n-hexane (5 ml)
  5. customcrystallization of the reaction product
  6. filtrationThe resulting product was recovered by filtration
  7. washwashed with n-hexan
  8. customdried

Sources & evidence

ORD record
ord-1d512c92792f43509a09120bf02ffcbe
Source dataset
uspto-grants-1982_08
Patent number
US04344944

Reaction notes

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