Hydrochloric Acid → HCID 15550462, compound

HRID 2288911Notes

Reaction equation

HRID 2288911 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 mmol). 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-8861d163aee446b9881374361de0d4af
Source dataset
uspto-grants-2000_07
Patent number
US06090843

Reaction notes

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