Sodium Iodide → 4-Nitro-3-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid phenylmethyl ester

HRID 1494259Notes

Reaction equation

HRID 1494259 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]([N+:45]([O-:47])=[O:46])=[C:41]([OH:48])[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]([N+:45]([O-:47])=[O:46])=[C:41]([O:48][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)[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 149864353-Hydroxy-4-nitrobenzoic acid benzyl ester

Product 1

HCID 149864364-Nitro-3-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid phenylmethyl esterYield 64.9%

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 3-hydroxy-4-nitrobenzoic acid phenylmethyl ester, 3.5 g (0.026 mol) of anhydrous 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 42 hours. Workup as described in example 16 and purification by HPLC using 10% ethyl acetate-hexane gave 5.45 g of 4-nitro-3-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid phenylmethyl ester as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 42 hours
  3. customWorkup as described in example 16 and purification by HPLC

Sources & evidence

ORD record
ord-2c7237f2237748b6a65202c925b5d137
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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