1-Iodohexane → HCID 14986433, compound

HRID 1613084Notes

Reaction equation

HRID 1613084 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[C:18]([OH:25])[C:17]=1[CH2:26][CH2:27][CH3:28].[CH2:29](I)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:29]([O:21][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][C:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]=2[OH:1])=[C:17]([CH2:26][CH2:27][CH3:28])[C:18]=1[OH:25])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 516892Sodium BicarbonateHCID 14986310HCID 14986310, compound

Product 1

HCID 14986433HCID 14986433, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.00 g (2.57 mmol) of 4-[6-(2,3-dihydroxyphenyl)hexyloxy]-2-hydroxy-3-propylbenzoic acid, 0.76 mL (5.15 mmol) of n-hexyl iodide and 0.26 g (3.36 mmol) of sodium bicarbonate in 15 mL of anhydrous dimethylformamide was stirred and heated at 70° for 16 hours. The solvent was removed on the oil pump, water was added and the product was extracted with ethyl acetate. The dried extract was concentrated under reduced pressure to an oil which was purified by chromatography on silica gel using 5% ethyl acetate-toluene to give 1.01 g (83% yield) of 4-[6-(2,3-dihydroxyphenyl)hexyloxy]-2-hydroxy-3-propylbenzoic acid hexyl ester as an oil.

Workup

  1. temperatureheated at 70° for 16 hours
  2. customThe solvent was removed on the oil pump, water
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated under reduced pressure to an oil which
  7. customwas purified by chromatography on silica gel using 5% ethyl acetate-toluene

Sources & evidence

ORD record
ord-4bb51ea03a204da78defeb6a25388b93
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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