1,1-Dibromoethane → 1,2-Diphenyl-1-[4-(2-bromoethoxy)phenyl]-1-buten-4-ol

HRID 2396134Notes

Reaction equation

HRID 2396134 reaction equation
[C:1]1(/[C:7](/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[C:8](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:25][CH:26](Br)[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]1([C:7]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:27][CH2:26][Br:25])=[CH:22][CH:23]=2)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 13298065Z-4-(4-hydroxy-1,2-diphenyl-but-1-enyl)-phenol

Product 1

HCID 544646161,2-Diphenyl-1-[4-(2-bromoethoxy)phenyl]-1-buten-4-ol

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture containing 31,6 g of (Z)-1,2-diphenyl-1-(4-hydroxyphenyl)-1-buten-4-ol, 93,9 g of dibromoethane, 20,7 g of anhydrous potassium carbonate and 250 ml of methyl ethyl ketone is refluxed for 24 h. The inorganic salts are removed by filtration followed by evaporating the solvent and recrystallizing frommethanol. The yield is 17,3 g (41%) and m.p. 133°-7° C.

Workup

  1. temperatureis refluxed for 24 h
  2. customThe inorganic salts are removed by filtration
  3. customby evaporating the solvent
  4. customrecrystallizing frommethanol

Sources & evidence

ORD record
ord-ca650d11455a4e3f8e8c46b6eea5dec0
Source dataset
uspto-grants-1996_02
Patent number
US05491173

Reaction notes

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