Water → HCID 58609394, compound

HRID 1257128Notes

Reaction equation

HRID 1257128 reaction equation
[OH-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O>CN(C=O)C.C1COCC1.C(OCC)(=O)C.ClCCl>[I:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][OH:18])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 962WaterHCID 108944-IodophenolHCID 14798Sodium HydroxideHCID 21981760Bromohexanol

Product 1

HCID 58609394HCID 58609394, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of NaOH (0.327 g, 8.18 mmol) and 4-iodophenol (1.5 g, 6.82 mmol) in 7.5 ml of DMF and 3.5 ml of THF was stirred at room temperature for 15 minutes. Then bromohexanol (1.482 g, 8.18 mmol) was added and the reaction mixture was warmed at 60° C. When the reaction is over, water was added (15 ml) and the mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and after filtration the solvent was removed at reduced pressure. The product was isolated by silica gel column chromatography using a mixture of ethyl acetate:dichloromethane 3:7 as eluant. A white solid was obtained (1.509 g, yield 69%).

Workup

  1. additionwas added (15 ml)
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. filtrationafter filtration the solvent
  5. customwas removed at reduced pressure
  6. customThe product was isolated by silica gel column chromatography
  7. customA white solid was obtained (1.509 g, yield 69%)

Sources & evidence

ORD record
ord-4d54082da2264dfb878070b3c2569fe4
Source dataset
uspto-grants-2013_06
Patent number
US08461354B2

Reaction notes

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