Sodium Hydroxide → HCID 9929026, compound

HRID 2392948Notes

Reaction equation

HRID 2392948 reaction equation
C([O:3][C:4](=[O:29])/[CH:5]=[C:6](\[CH3:28])/[CH:7]=[CH:8]/[C:9]1[CH2:13][CH2:12][CH2:11][C:10]=1[C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)C.[OH-].[Na+]>C1COCC1.CCO>[CH3:28]/[C:6](/[CH:7]=[CH:8]/[C:9]1[CH2:13][CH2:12][CH2:11][C:10]=1[C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)=[CH:5]\[C:4]([OH:29])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9908547HCID 9908547, compound

Product 1

HCID 9929026HCID 9929026, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.32 g of (2E,4E)-3-Methyl-5-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopent-1-enyl]-penta-2,4-dienoic acid ethyl ester was dissolved in 13 ml of THF/EtOH=1/1 and treated with 5.6 ml of 3N NaOH. The mixture was kept for 48 h at ambient temperature and then poured onto crushed ice/HCI. Extraction with AcOEt, washing with H2O, drying over Na2 SO4, evaporation of the solvent, and recrystallization from AcOEt afforded 803 mg of the title compound as yellow crystals of mp. 195°-196°(dec.).

Workup

  1. additionpoured
  2. customonto crushed ice/HCI
  3. extractionExtraction with AcOEt
  4. washwashing with H2O
  5. dry with materialdrying over Na2 SO4, evaporation of the solvent, and recrystallization from AcOEt

Sources & evidence

ORD record
ord-18badb7e169e4def85b205b986a4294a
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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