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

HRID 894985Notes

Reaction equation

HRID 894985 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

A mixture of 6,7-dihydroxychromone-3-carboxylic acid (888 mg, 4 mmol) and thionyl chloride (25 ml) was refluxed for one hour and the thionyl chloride was evaporated. After the addition of benzene, the mixture was evaporated again to dryness and the residue was triturated with dichloromethane to give the desired compound (719 mg).

Workup

  1. temperaturewas refluxed for one hour
  2. customthe thionyl chloride was evaporated
  3. additionAfter the addition of benzene
  4. customthe mixture was evaporated again to dryness
  5. customthe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-28324460acf34701b013aa657da992b0
Source dataset
uspto-grants-1981_08
Patent number
US04285940

Reaction notes

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