Sodium Hydroxide → HCID 19710644, compound

HRID 726179Notes

Reaction equation

HRID 726179 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH:11]=[CH:10]2)=[O:4].[OH-].[Na+]>C(O)C>[S:13]1[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])[CH:10]=[CH:11][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23291432HCID 23291432, compound

Product 1

HCID 19710644HCID 19710644, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Methyl-2H-thiochromene-8-carboxylate (0.300 g, 1.46 mmol) was dissolved in ethanol (5 ml) and treated with 10% sodium hydroxide solution (10 ml). The mixture was then heated to reflux with stirring. After 5 h, the reaction mixture was allowed to cool The ethanol present was then removed by evaporation under reduced pressure. The aqueous residue was then washed with CH2Cl2 (2x) before being acidified to pH1 using 5M HCl. The resultant pale yellow precipitate was then filtered off and dried in vacuo to give the title compound (0.195 g, 69%) as a pale yellow solid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux
  3. custompresent was then removed by evaporation under reduced pressure
  4. washThe aqueous residue was then washed with CH2Cl2 (2x)
  5. filtrationThe resultant pale yellow precipitate was then filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e551cc2ee1c74dc5bf217ae47727ac41
Source dataset
uspto-grants-1998_01
Patent number
US05708174

Reaction notes

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