Sodium Hydroxide → HCID 332828, compound

HRID 1243516Notes

Reaction equation

HRID 1243516 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-fafa68ca9b174757bc17db4bd37047d5
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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