Ethanol → HCID 15346529, compound

HRID 440126Notes

Reaction equation

HRID 440126 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][CH:7]([C:11]([OH:13])=[O:12])[C:6]=2[CH:14]=1.S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][CH:7]([C:11]([O:13][CH2:20][CH3:21])=[O:12])[C:6]=2[CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13953802HCID 13953802, compound

Product 1

HCID 15346529HCID 15346529, compound

Procedure

A mixture of 6-chloro-3,4-dihydro-2H-1-benzothiopyran-4-carboxylic acid (12.56 g, 0.055 mol) and concentrated sulfuric acid (20 mL) in ethanol is heated at reflux for 29 hours, cooled, concentrated in vacuo and diluted with a water/methylene chloride mixture. The aqueous phase is separated and extracted with methylene chloride. The organic phase and organic extracts are combined, dried, decolorized with activated carbon and concentrated in vacuo to give the title product as a pale yellow oil (12.34 g) which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 29 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additiondiluted with a water/methylene chloride mixture
  6. customThe aqueous phase is separated
  7. extractionextracted with methylene chloride
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68bcf69be009437fa8221817a28b26e2
Source dataset
uspto-grants-1996_05
Patent number
US05516918

Reaction notes

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