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

HRID 894982Notes

Reaction equation

HRID 894982 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 chlorideYield 93.4%

Procedure

A mixture of 6,7-dihydroxychromone-3-carboxylic acid (9.0 g, 4 mmol) and thionyl chloride (150 ml) was refluxed for 45 minutes and the thionyl chloride was evaporated. After the addition of benzene, the mixture was evaporated again to dryness and the residue was triturated with n-hexane to afford the desired compound (9.1 g, 93.4%).

Workup

  1. temperaturewas refluxed for 45 minutes
  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 n-hexane

Sources & evidence

ORD record
ord-116ccc2ab25c488290a07b55c7ee64d8
Source dataset
uspto-grants-1981_08
Patent number
US04285939

Reaction notes

Loading…