Sodium Hydroxide → HCID 54173080, compound

HRID 2395396Notes

Reaction equation

HRID 2395396 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([O-:22])=[O:21])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 73473900HCID 73473900, compound

Product 1

HCID 54173080HCID 54173080, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (335 mg, 0.951 mmol, 1.0 eq) methyl, 3-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]ethenyl]benzoate in 8 ml methanol and 1.9 ml (1.90 mmol, 2.0 eq) of 1N NaOH was heated to reflux for 1.5 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, poured into 100 ml H2O, basified to pH 12, and washed once with ethyl acetate. The aqueous layer was acidified to pH 4 and extracted three times with ethyl acetate. The ethyl acetate extracts were combined, washed once with H2O, once with brine, dried over NA2SO4, and concentrated to yield 295 mg of white waxy crystals. Recrystallization from ethyl acetate-hexane afforded 100 mg, 34%/, of the cis isomer as white crystals. M.P.: 93°-94° C. Elemental Analysis: Calc'd for C21H22O4 : Calc'd: C, 74.53; H, 6.55. Found: C, 74.32; H, 6.68.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. concentrationconcentrated in vacuo
  4. additionpoured into 100 ml H2O
  5. washwashed once with ethyl acetate
  6. extractionextracted three times with ethyl acetate
  7. washwashed once with H2O, once with brine
  8. customdried over NA2SO4
  9. concentrationconcentrated
  10. customto yield 295 mg of white waxy crystals
  11. customRecrystallization from ethyl acetate-hexane
  12. customafforded 100 mg, 34%/, of the cis

Sources & evidence

ORD record
ord-9cb5072d0bff4581bdc49a1d2d50cf44
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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