Sodium Hydroxide → HCID 86753063, compound

HRID 2392942Notes

Reaction equation

HRID 2392942 reaction equation
C([O:3][C:4](=[O:28])/[CH:5]=[C:6](\[CH3:27])/[CH:7]=[CH:8]/[C:9](/[Br:26])=[C:10](\[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)/[CH3:11])C.[OH-].[Na+]>CCO.C1COCC1>[Br:26]/[C:9](=[C:10](/[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)\[CH3:11])/[CH:8]=[CH:7]/[C:6](/[CH3:27])=[CH:5]/[C:4]([OH:28])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86753062HCID 86753062, compound

Product 1

HCID 86753063HCID 86753063, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

472 mg of (2E,4E,6E)-6-bromo-3-methyl-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid ethyl ester were dissolved in 10 ml of EtOH/THF=1:1 and treated with 2.65 ml of 2N aq. NaOH. The reaction mixture was stirred for 22 hours at ambient temperature in the dark. It was then poured onto crushed ice, extracted with AcOEt, washed with brine and H2O, and dried over Na2SO4. Evaporation of the solvent and twofold crystallization (hexane/AcOEt=8:2) yielded finally 168 mg of (2E,4E,6E)-6-bromo-3-methyl-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid as yellow crystals of m.p. 189°-190° C.

Workup

  1. additionIt was then poured
  2. customonto crushed ice
  3. extractionextracted with AcOEt
  4. washwashed with brine and H2O
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent and twofold crystallization (hexane/AcOEt=8:2)

Sources & evidence

ORD record
ord-fbe18dec3f954120b7cedb17835b01a1
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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