Sodium Hydroxide → HCID 23291416, compound

HRID 365396Notes

Reaction equation

HRID 365396 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][CH2:11][CH2:10]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])[CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86755873HCID 86755873, compound

Product 1

HCID 23291416HCID 23291416, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methylthiochroman-8-carboxylate (0.220 g, 1.05 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 (2×) 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 (0.156 g, 76%) (D6).

Workup

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

Sources & evidence

ORD record
ord-4edbe41fac814bf4b581065929cd5786
Source dataset
uspto-grants-2000_10
Patent number
US06127379

Reaction notes

Loading…