Ethanol → HCID 15346529, compound

HRID 1939156Notes

Reaction equation

HRID 1939156 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 paleyellow 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-eab646f4cb24424eb40a8f1a43016967
Source dataset
uspto-grants-1997_12
Patent number
US05696050

Reaction notes

Loading…