Potassium Iodide → Ethyl 11-(p-benzyloxyphenoxy)undecanoate

HRID 634595Notes

Reaction equation

HRID 634595 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].C(=O)([O-])[O-:49].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:49][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 235144Ethyl 11-bromoundecanoateHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 21259961Ethyl 11-(p-benzyloxyphenoxy)undecanoateYield 134.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 5000 ml flask equipped with a stirrer and a condenser were charged 400.2 g of hydroquinone monobenzyl ether, 586.5 g of ethyl 11-bromoundecanoate, 331.7 g of anhydrous potassium carbonate, 33.2 g of potassium iodide and 1500 ml of N,N-dimethylformamide (DMF), and the mixture was refluxed for 6 hours. This solution was poured into 2000 ml of ice-water to precipitate white crystals. The precipitated crystals were collected by filtration, washed with distilled water and recrystallized from ethanol to obtain 535.5 g of the title compound.

Workup

  1. customIn a 5000 ml flask equipped with a stirrer and a condenser
  2. temperaturethe mixture was refluxed for 6 hours
  3. customto precipitate white crystals
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with distilled water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8f40e7da651145b2b3825d3b0fe82d50
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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