Sodium Hydroxide → HCID 16224656, compound

HRID 2392945Notes

Reaction equation

HRID 2392945 reaction equation
C([O:3][C:4](=[O:27])/[CH:5]=[C:6](\[CH3:26])/[CH:7]=[CH:8]/[CH:9]1[CH2:11][CH:10]1[C:12]1[CH:21]=[CH:20][C:19]2[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=2[CH:13]=1)C.[OH-].[Na+]>C1COCC1.CCO>[CH3:26]/[C:6](/[CH:7]=[CH:8]/[CH:9]1[CH2:11][CH:10]1[C:12]1[CH:21]=[CH:20][C:19]2[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=2[CH:13]=1)=[CH:5]\[C:4]([OH:27])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86753064HCID 86753064, compound

Product 1

HCID 16224656HCID 16224656, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

8.84 g of (2E,4E)-3-methyl-5-[(1RS,2RS)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropyl]-penta-2,4-dienoic acid ethyl ester (ca. 94% pure according to 1H-NMR) was dissolved in 100 ml of THF/EtOH=1:1 and treated with 40 ml of 3N aq. NaOH. The reaction mixture was kept in the dark at ambient temperature for three days. It was then poured onto crashed ice, extracted with EtOEt, washed with H2O, and dried over Na2SO4. Evaporation of the solvent and twofold crystallisation (hexane/AcOEt=8:2 and 7:3) yielded 4.25 g of (2E,4E)-3-methyl-5-[(1RS,2RS)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropyl]-penta-2,4-dienoic acid as white crystals of m.p. 150°-151° C.

Workup

  1. customdark at ambient temperature
  2. customfor three days
  3. additionIt was then poured
  4. extractionextracted with EtOEt
  5. washwashed with H2O
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent and twofold crystallisation (hexane/AcOEt=8:2 and 7:3)

Sources & evidence

ORD record
ord-809b9c6612ca42068662d2d0e0564eea
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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