Sodium Hydroxide → HCID 18317426, compound

HRID 1700521Notes

Reaction equation

HRID 1700521 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[C:11](=[O:21])[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][C:9]=2[O:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1>[C:4]([C:6]1[C:10]2[C:11](=[O:21])[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][C:9]=2[O:8][CH:7]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 183177573-Ethoxycarbonyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one

Product 1

HCID 18317426HCID 18317426, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (10 ml) was dissolved 3-ethoxycarbonyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.71 g). To the solution was added 1N sodium hydroxide (5.0 ml), and the mixture was stirred at room temperature overnight (12 hours). The reaction solution was concentrated under reduced pressure, and to the residue was added potassium hydrogensulfate to make the mixture acidic. To the mixture was added ethyl acetate, and the mixture was subjected to extraction. The upper layer was washed with saturated brine, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure, and the residue was washed with isopropylether to give 3-carboxy-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.59 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added potassium hydrogensulfate
  3. additionTo the mixture was added ethyl acetate
  4. extractionthe mixture was subjected to extraction
  5. washThe upper layer was washed with saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. washthe residue was washed with isopropylether

Sources & evidence

ORD record
ord-8694f1d6f9d1454e9a682b2f3ef91ec4
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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