Thionyl Chloride → 6,7-dihydroxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride

HRID 358445Notes

Reaction equation

HRID 358445 reaction equation
[OH:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([C:12](O)=[O:13])=[CH:7][C:6]=2[CH:15]=1.S(Cl)([Cl:19])=O>CN(C)C=O>[OH:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([C:12]([Cl:19])=[O:13])=[CH:7][C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 139895536,7-Dihydroxycoumarin-3-carboxylic Acid

Product 1

HCID 212867876,7-dihydroxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 6,7-dihydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid (110 mg), thionyl chloride (5 mL), and dimethylformamide (one drop) was stirred for 2 hours at room temperature. The excess thionyl chloride was distilled off in vacuo. Benzene (20 mL) was added, followed by vacuum distillation and vacuum drying, to yield 6,7-dihydroxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride.

Workup

  1. distillationThe excess thionyl chloride was distilled off in vacuo
  2. additionBenzene (20 mL) was added
  3. distillationfollowed by vacuum distillation and vacuum
  4. customdrying

Sources & evidence

ORD record
ord-863a20bb54bf471d93e5e18abcfbc03b
Source dataset
uspto-grants-1984_08
Patent number
US04468394

Reaction notes

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