Thionyl Chloride → 7,8-dihydroxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride

HRID 358447Notes

Reaction equation

HRID 358447 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]=[C:7]([C:11](O)=[O:12])[C:8](=[O:10])[O:9][C:4]=2[C:3]=1[OH:16].S(Cl)([Cl:19])=O>>[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]=[C:7]([C:11]([Cl:19])=[O:12])[C:8](=[O:10])[O:9][C:4]=2[C:3]=1[OH:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 151737117,8-Dihydroxy-3-carboxy-coumarin

Product 1

HCID 151737127,8-dihydroxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride

Procedure

7,8-Dihydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid (50 mg) was heated under reflux for 5.5 hours in thionyl chloride (20 mL), and then thionyl chloride was distilled off. Benzene (10 mL) was added to the residues, and the benzene was distilled off, followed by vacuum drying, to yield 7,8-dihydroxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride.

Workup

  1. distillationthionyl chloride was distilled off
  2. additionBenzene (10 mL) was added to the residues
  3. distillationthe benzene was distilled off
  4. customdrying

Sources & evidence

ORD record
ord-b0a775df336e4d44aac03a3342aa5a5f
Source dataset
uspto-grants-1984_08
Patent number
US04468394

Reaction notes

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