Potassium Iodide → HCID 15233477, compound

HRID 1492839Notes

Reaction equation

HRID 1492839 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:45]=1[O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([O:35][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH2:51][C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C:45]=3[O:58][CH2:59][C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 15233477HCID 15233477, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (3 mmol) of 3-hydroxy-5-(octadecyloxy) benzoic acid phenylmethyl ester, 1.6 g (3.4 mmol) of 1-(6-bromo-hexyl)-2,3-bis(phenylmethoxy)benzene [M. Carson, R.-J. Han and R. A. LeMahieu, U.S. Pat. No. 5,025,036 (1991)], 0.45 g (3 mmol) of potassium iodide and 0.84 g (6 mmol) of potassium carbonate in 40 ml of acetone and 10 ml of DMF was stirred at reflux for 47 hours. The solvents were removed at reduced pressure and the residue was purified by HPLC using 5% ethyl acetate-hexane to give 2.0 g (77% yield) of 3-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester as an oil. The nmr spectrum served to confirm the structure.

Workup

  1. temperatureat reflux for 47 hours
  2. customThe solvents were removed at reduced pressure
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-e4e2c8bbc33e4334ba63ac9ced579303
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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