Thionyl Chloride → 6,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-carbonyl chloride

HRID 1649124Notes

Reaction equation

HRID 1649124 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH:7]=[C:6]([C:13](O)=[O:14])[C:5]2=[O:16].S(Cl)([Cl:19])=O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH:7]=[C:6]([C:13]([Cl:19])=[O:14])[C:5]2=[O:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 122007766,7-Dihydroxychromon-3-carboxylic acid

Product 1

HCID 127657576,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-carbonyl chloride

Procedure

6,7-Dihydroxychromon-3-carboxylic acid (888 mg) together with thionyl chloride (25 ml) were refluxed for one hour. Any unreacted thionyl chloride was then removed from the reaction mixture by distillation. Benzene was added to the residue, and the mixture was subjected to distillation. The residue was triturated with dichloromethane to obtain the desired product (719 mg).

Workup

  1. customAny unreacted thionyl chloride was then removed from the reaction mixture by distillation
  2. additionBenzene was added to the residue
  3. distillationthe mixture was subjected to distillation
  4. customThe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-d7e05b2f497b4a1e9e3a50ae7b7835a9
Source dataset
uspto-grants-1983_11
Patent number
US04415567

Reaction notes

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