Sodium Iodide → HCID 14986439, compound

HRID 1613086Notes

Reaction equation

HRID 1613086 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]1([CH2:36][O:37][C:38](=[O:49])[C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([N+:46]([O-:48])=[O:47])[CH:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C)C=O>[C:30]1([CH2:36][O:37][C:38](=[O:49])[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:9]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:41]([N+:46]([O-:48])=[O:47])[CH:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 14986438HCID 14986438, compound

Product 1

HCID 14986439HCID 14986439, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.8 g (0.013 mol) of 1-(6-bromohexyl)-2,3-bis(phenylmethoxy)benzene, 3.5 g (0.013 mol) of 4-hydroxy-3-nitrobenzoic acid phenylmethyl ester, 3.5 g (0.026 mol) of potassium carbonate and 2.9 g (0.019 mol) of sodium iodide in 125 mL of acetone and 13 mL of dimethylformamide was stirred and heated at reflux for 5 days. Workup as described in Example 16 and purification by HPLC using 50% methylene chloride-hexane gave 6.85 g (83% yield) of 3-nitro-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid phenylmethyl ester as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 days
  3. customWorkup as described in Example 16 and purification by HPLC

Sources & evidence

ORD record
ord-417887e1ee3d469c8beae6dbf192a08f
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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