Hydrochloric Acid → HCID 23116272, compound

HRID 499874Notes

Reaction equation

HRID 499874 reaction equation
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[C:5]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:4]=1[CH2:21][C:22]([O:24]C)=[O:23])[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[C:5]([C:11](=[O:20])[C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:4]=1[CH2:21][C:22]([OH:24])=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11995808HCID 11995808, compound

Product 1

HCID 23116272HCID 23116272, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 8 (0.18 g, 0.53 mmol) obtained in Example 8 was dissolved in methanol (1.5 mL), and a 2 mol/L aqueous solution of sodium hydroxide (1.5 mL) was added thereto. The mixture was stirred at room temperature for 6 hours, and then stirred at 50° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was made acidic by addition of 4 mol/L hydrogen chloride (3.0 mL), followed by extraction with chloroform (50 mL×3). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 2-ethyl-3,5-dihydroxy-6-(4-methoxybenzoyl)phenylacetic acid (0.17 g, 0.52 mmol).

Workup

  1. stirringstirred at 50° C. for 1.5 hours
  2. temperatureAfter cooling to room temperature
  3. extractionfollowed by extraction with chloroform (50 mL×3)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0005866998fd406cbbb598b6ccdd1905
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Reaction notes

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