Hydrochloric Acid → HCID 15550462, compound

HRID 1596485Notes

Reaction equation

HRID 1596485 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22]C)=[O:21])=[CH:14][CH:13]=3)=[O:11])=[C:8]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[S:7][C:6]=2[CH:31]=1.[OH-].[Na+].Cl>CO.[Cl-].[Na+].O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:17]=3)=[O:11])=[C:8]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[S:7][C:6]=2[CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15550461HCID 15550461, compound

Product 1

HCID 15550462HCID 15550462, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl][4-carbomethoxymethoxyphenyl]methanone (132 mg, 0.30 mmol) stirring in methanol (5 mL) was added sodium hydroxide (0.43 mL of a 5 N aqueous solution, 2.13 nmol). The red mixture was heated to reflux for 0.5 hour, cooled to room temperature, and made acidic with hydrochloric acid (0.70 mL of a 5N aqueous solution). The mixture was then poured into brine and extracted with ethyl acetate. The combined organic extracts were washed thoroughly with brine, dried (magnesium sulfate), and filtered. Concentration afforded the title compound as a yellow solid.

Workup

  1. temperatureThe red mixture was heated
  2. temperatureto reflux for 0.5 hour
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed thoroughly with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationConcentration

Sources & evidence

ORD record
ord-b5016d9fbe1a4e68857008dc0e305888
Source dataset
uspto-grants-2001_09
Patent number
US06291484B1

Reaction notes

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