Sodium Hydroxide → HCID 22373193, compound

HRID 1603272Notes

Reaction equation

HRID 1603272 reaction equation
C([O:3][C:4](=[O:26])/[CH:5]=[C:6](\[CH3:25])/[CH:7]=[CH:8]/[C:9]1[CH2:13][CH2:12][CH2:11][C:10]=1[C:14]#[C:15][C:16]1[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]=1[CH3:24])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:25]/[C:6](/[CH:7]=[CH:8]/[C:9]1[CH2:13][CH2:12][CH2:11][C:10]=1[C:14]#[C:15][C:16]1[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]=1[CH3:24])=[CH:5]\[C:4]([OH:26])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86754817HCID 86754817, compound

Product 1

HCID 22373193HCID 22373193, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

(2E,4E)-3-Methyl-5-[2-(2,6,6-trimethyl-cyclohex-1-enylethynyl)-cyclopent-1-enyl]-penta-2,4-dienoic acid ethyl ester (1. 47 g) was dissolved in 14 ml of THF/EtOH=1/1. 3N aqueous NaOH (7.0 ml) was added and the reaction flask kept in the dark. After stirring for 16 hours at ambient temperature, the mixture was poured onto crushed ice/HCl, extracted twice with EtOEt, washed with water, dried over Na2SO4, and evaporated to dryness. Crystallization from EtOEt/pentane afforded 1.31 g of (2E,4E)-3-Methyl-5-[2-(2,6,6-trimethyl-cyclohex-1-enylethynyl)-cyclopent-1-enyl] -penta-2,4-dienoic acid as yellow crystals of mp. 173-174° C.

Workup

  1. additionthe mixture was poured
  2. extractionextracted twice with EtOEt
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customCrystallization from EtOEt/pentane

Sources & evidence

ORD record
ord-2e58b0d2cbb54e75b273a93176ae0a78
Source dataset
uspto-grants-1999_11
Patent number
US05986131

Reaction notes

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