Potassium Iodide → HCID 14986328, compound

HRID 1494226Notes

Reaction equation

HRID 1494226 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][C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:9]=1[O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.[C:34]1([CH2:40][O:41][C:42](=[O:54])[C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[C:45]([CH2:50][CH2:51][CH3:52])[C:44]=2[OH:53])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:34]1([CH2:40][O:41][C:42](=[O:54])[C:43]2[CH:48]=[CH:47][C:46]([O:49][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][C:15](=[O:23])[C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)[C:9]=3[O:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[C:45]([CH2:50][CH2:51][CH3:52])[C:44]=2[OH:53])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14986286HCID 14986286, compoundHCID 14986292HCID 14986292, compound

Product 1

HCID 14986328HCID 14986328, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.91 g (3.75 mmol) of 1-(6-bromohexyl)-2,3-bis[(4-methylbenzoyl)oxy]benzene, 1.07 g (3.75 mmol) 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester, 0.94 g (5.63 mmol) of potassium iodide and 0.75 g (5.63 mol) of potassium carbonate in 40 mL of acetone was stirred at reflux for 26 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by HPLC using 5% ethyl acetate-hexane to give 0.85 g (32% yield) of 2-hydroxy-4-[6-[2,3-bis[(4-methylbenzoyl)oxy]phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester as an oil.

Workup

  1. temperatureat reflux for 26 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-fa751503241c42a5bfa968ca931e4147
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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