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

HRID 982442Notes

Reaction equation

HRID 982442 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 from methanol. 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 from methanol

Sources & evidence

ORD record
ord-779fa5d296e14f008aece5d991d133c1
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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