Ethanol → HCID 10207974, compound

HRID 984937Notes

Reaction equation

HRID 984937 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([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:8]=1)C.C(O)C.O>[OH-].[Na+]>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=2)=[CH:15][CH2:14][O:13][C:9]2[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:31])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 9893607HCID 9893607, compound

Product 1

HCID 10207974HCID 10207974, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-{3-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic acid ethyl ester (example 1) (755 mg, 1.4 mmol) was hydrolysed in 1N NaOH (5.6 ml) and ethanol (15 ml) for 16 h at room temperature. Water (5 ml) was added and ethanol removed by concentration in vacuo. The mixture was neutralised with 6N HCl. The crude product was extracted with ethyl acetate (×3). The organic layers were combined, dried (MgSO4) and evaporated. The residue was dissolved in toluene and the title compound precipitated with petroleum ether, to give 430 mg of the title compound.

Workup

  1. customethanol removed by concentration in vacuo
  2. extractionThe crude product was extracted with ethyl acetate (×3)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in toluene
  6. customthe title compound precipitated with petroleum ether

Sources & evidence

ORD record
ord-e966d0e1084242dea462f4f798bb7798
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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