Sodium Hydroxide → HCID 332828, compound

HRID 585551Notes

Reaction equation

HRID 585551 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH:15]([C:16]([O:18]CC)=[O:17])C(O)(C)CC(=O)[CH:11]3[C:24]([O:26]CC)=[O:25])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([CH2:11][C:24]([OH:26])=[O:25])[CH2:15][C:16]([OH:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 223050Diethyl 2-(1,3-benzodioxol-5-yl)-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylate

Product 1

HCID 332828HCID 332828, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 2-(1,3-benzodioxol-5-yl)-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylate (19 g) was suspended in ethanol (140 ml) and an aqueous solution of NaOH (50%, 270 ml). The mixture was heated at reflux for one hour. After the mixture was cooled to room temperature, the ethanol was removed under reduced pressure. Then, concentrated HCl was added until pH 1 was achieved while maintaining the temperature below 50° C. The mixture was filtered. The solid was washed with ether. The two layers were separated. The aqueous layer was extracted with ether (3×). The ether layers were combined, dried, and concentrated to give product. 1H NMR (DMSO-d6) δ 12.06 (br s, 2H), 6.88-6.68 (m, 3H), 5.98 (s, 2H), 3.4-3.3 (m, 1H), 2.62-2.42 (m, 4H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. customthe ethanol was removed under reduced pressure
  4. additionThen, concentrated HCl was added until pH 1
  5. temperaturewhile maintaining the temperature below 50° C
  6. filtrationThe mixture was filtered
  7. washThe solid was washed with ether
  8. customThe two layers were separated
  9. extractionThe aqueous layer was extracted with ether (3×)
  10. customdried
  11. concentrationconcentrated
  12. customto give product

Sources & evidence

ORD record
ord-30f32ee1b42a465fb7859fec82c33dcc
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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