Sodium Iodide → HCID 15233464, compound

HRID 1492829Notes

Reaction equation

HRID 1492829 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[CH:5]=1.Br[CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.[I-].[Na+].[C:32](=[O:35])([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([O:11][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH:7]=[C:8]([O:10][CH2:16][CH2:15][CH2:14][O:35][C:32]2[CH:26]=[CH:25][C:24]([C:21]3[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=3)=[CH:29][CH:28]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 152334631,1'-Biphenyl, 4-(3-bromopropoxy)-

Product 1

HCID 15233464HCID 15233464, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.79 g (4.7 mmol) of 3,5-dihydroxybenzoic acid methyl ester, 3.0 g (10.3 mmol) of 4-(3-bromopropoxy)-1,1-biphenyl, 1.55 g (10.3 mmol) of sodium iodide and 3.9 g (28 mmol) of potassium carbonate in 80 mL of anhydrous acetone and 40 mL of DMF was stirred at reflux for 39 hours. The solvents were removed at reduced pressure, water was added to the residue and the product was extracted with chloroform. The dried extract was concentrated to a solid which was purified by chromatography on 90 g of silica gel using chloroform to give 1.5 g (54% yield, mp 142°-145°) of 3,5-bis [3-(1,1'-biphenyl-4-yloxy)propoxy]benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 39 hours
  2. customThe solvents were removed at reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with chloroform
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by chromatography on 90 g of silica gel

Sources & evidence

ORD record
ord-4a776545cb2744af928a3b0b3b6478a6
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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