Sodium Iodide → HCID 14986442, compound

HRID 1494262Notes

Reaction equation

HRID 1494262 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH3:19])[C:9]=1[O:20][CH3:21].[C:22]1([CH2:28][O:29][C:30](=[O:42])[C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([CH2:38][CH2:39][CH3:40])[C:32]=2[OH:41])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C)C=O>[C:22]1([CH2:28][O:29][C:30](=[O:42])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH3:19])[C:9]=3[O:20][CH3:21])=[C:33]([CH2:38][CH2:39][CH3:40])[C:32]=2[OH:41])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14986292HCID 14986292, compoundHCID 149864411-(6-Bromohexyl)-2,3-dimethoxy-4-(1,1-dimethylethyl)benzene

Product 1

HCID 14986442HCID 14986442, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.0 g (11.2 mmole) of 1-(6-bromohexyl)-2,3-dimethoxy-4-(1,1-dimethylethyl)benzene, 3.2 g (11.2 mmole) of 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester, 3.1 g (22.4 mmole) of potassium carbonate and 1.7 g (11.2 mmole) of sodium iodide in 70 mL of anhydrous acetone and 7 mL of anhydrous dimethylformamide was stirred at reflux for 31 hours. Workup as in Example 16 and purification by HPLC using 5% ethyl acetate-hexane gave 5.3 g, (84% yield) of 2-hydroxy-4-[6-[2,3-dimethoxy-4-(1,1-dimethylethyl)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester as an oil.

Workup

  1. temperatureat reflux for 31 hours
  2. customWorkup as in Example 16 and purification by HPLC

Sources & evidence

ORD record
ord-c434d4725ec7466abc83291a24264aa7
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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