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

HRID 1105533Notes

Reaction equation

HRID 1105533 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

The compound (57.3 mg) obtained in Example 5 was dissolved in 10 ml of benzene, and with stirring at room temperature, 0.5 ml of thionyl chloride was added. The mixture was refluxed for 3 hours with stirring. The reaction mixture was concentrated, and 5 ml of n-hexane was added to the concentrate to crystallize it. The resulting crystals were collected by filtration, washed with n-hexane and dried to afford 34.8 mg of the desired product.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. stirringwith stirring
  3. concentrationThe reaction mixture was concentrated
  4. addition5 ml of n-hexane was added to the
  5. concentrationconcentrate
  6. customto crystallize it
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-cd2d912029eb4d2d90935399b209fd23
Source dataset
uspto-grants-1982_01
Patent number
US04309354

Reaction notes

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