Thionyl Chloride → HCID 20150387, compound

HRID 568736Notes

Reaction equation

HRID 568736 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH2:12][C:13](O)=[O:14])([CH3:11])[CH2:8][CH2:7][C:6]=2[CH:16]=1.S(Cl)([Cl:19])=O>CN(C)C=O.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH2:12][C:13]([Cl:19])=[O:14])([CH3:11])[CH2:8][CH2:7][C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20150416(6-Chloro-2-methyl-3,4-dihydro-2H-chromen-2-yl)acetic acid

Product 1

HCID 20150387HCID 20150387, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

To a solution composed of 2.89 g of (6-chloro-3,4-dihydro-2-methyl-2H-benzopyran-2-yl)acetic acid, 2 drops of N,N-dimethylformamide and 50 ml of benzene was added 0.9 ml of thionyl chloride and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was evaporated under reduced pressure to remove the low-boiling substances. The above procedure gave (6-chloro-3,4-dihydro-2-methyl-2H-benzopyran-2-yl)acetyl chloride in a quantitative yield of 3.1 g.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under reduced pressure
  4. customto remove the low-boiling substances

Sources & evidence

ORD record
ord-fd995710d19d464c9100841645fdfe90
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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