Sodium Hydroxide → HCID 22282607, compound

HRID 2085339Notes

Reaction equation

HRID 2085339 reaction equation
S1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:3][CH2:2]1.O[O:22][S:23]([O-:25])=O.[K+].[OH-].[Na+]>CO.O>[O:22]=[S:23]1(=[O:25])[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)=[CH:3][CH2:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 22282620HCID 22282620, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22282607HCID 22282607, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 4-(2H-1-benzothiopyran-4-yl)benzoate from reaction 33b (0.77 g, 2.75 mmol) was dissolved in methanol (30 mL) cooled to 0° C. and Oxone® (6.76 g, 11.1 mmol) in water (7 mL) was added. The reaction was stirred for 1 h at 0° C. and then allowed to warm to room temperature and stir for another hour. The reaction was diluted with water, pH adjusted to pH=8 with 1 N sodium hydroxide. This was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate and concentrated to give methyl 4-(1,1-dioxido-2H-1-benzothiopyran-4-yl)benzoate (0.784 g, 91%) as a solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir for another hour
  3. extractionThis was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bce0077863d455aad666bf1edec9561
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

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