Sodium Hydroxide → 3-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic acid

HRID 984940Notes

Reaction equation

HRID 984940 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:24]2[CH:25]=[CH:26][C:27]([Br:30])=[CH:28][CH:29]=2)=[CH:15][CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:31])=[O:3])=[CH:8][CH:9]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 102092253-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic Acid Ethyl Ester

Product 1

HCID 101861233-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic acidYield 58.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-{4-[3,3-bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic acid ethyl ester (example 5) (1.0 g, 2.0 mmol) in toluene (20 mL) and ethanol (50 mL) was added 1N NaOH (10.0 mL) and the reaction mixture was stirred for 16 h at room temperature. The reaction mixture was concentrated in vacuo and 1N HCl added. The product was extracted with ethyl acetate (x 3). The organic layers were combined, washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was recrystalised from warm ethanol (100 mL), witch was concentrated to 60 mL, and cooled, to give 600 mg (56%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and 1N HCl
  2. additionadded
  3. extractionThe product was extracted with ethyl acetate (x 3)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystalised
  9. temperaturefrom warm ethanol (100 mL), witch
  10. concentrationwas concentrated to 60 mL
  11. temperaturecooled

Sources & evidence

ORD record
ord-2bdc8716f9da47f1b501f095c86362b3
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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