Thionyl Chloride → HCID 20448124, compound

HRID 358446Notes

Reaction equation

HRID 358446 reaction equation
[C:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]2[CH:9]=[C:10]([C:14](O)=[O:15])[C:11](=[O:13])[O:12][C:7]=2[C:6]=1[O:19][C:20](=[O:22])[CH3:21])(=[O:3])[CH3:2].S(Cl)([Cl:25])=O>CN(C)C=O.C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]2[CH:9]=[C:10]([C:14]([Cl:25])=[O:15])[C:11](=[O:13])[O:12][C:7]=2[C:6]=1[O:19][C:20](=[O:22])[CH3:21])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18954222HCID 18954222, compound

Product 1

HCID 20448124HCID 20448124, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 7,8-diacetoxy-2-oxo-2H-1-benzopyran-3-carboxylic acid (612 mg), thionyl chloride (0.5 mL), dimethylformamide (one drop), and benzene (40 mL) was refluxed for 1 hour and then concentrated to about 10 mL. Hexane (20 mL) was added and the separated precipitates were filtered off, followed by vacuum drying, to yield 7,8-diacetoxy-2-oxo-2H-1-benzopyran-3-carbonyl chloride (600 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated to about 10 mL
  3. additionHexane (20 mL) was added
  4. customthe separated precipitates
  5. filtrationwere filtered off
  6. customdrying

Sources & evidence

ORD record
ord-f19b4591fc30400092ac2bc24980fb81
Source dataset
uspto-grants-1984_08
Patent number
US04468394

Reaction notes

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