Iodoethane → HCID 14986447, compound

HRID 1613091Notes

Reaction equation

HRID 1613091 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])[CH:17]=1.C(=O)(O)[O-].[Na+].[CH2:31](I)[CH3:32]>CN(C)C=O>[CH2:31]([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])=[CH:17][C:18]=1[OH:25])[CH3:32]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 14986340HCID 14986340, compound

Product 1

HCID 14986447HCID 14986447, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (2.9 mmole) of 4-[6-(2,3-dihydroxyphenyl)hexyloxy]-2-hydroxybenzoic acid, 0.295 g (3.5 mmole) of sodium bicarbonate and 2.4 mL (29 mmole) of ethyl iodide in 10 ml of anhydrous dimethylformamide was stirred at 50° for 6 hours. The solvent was removed on the oil pump and the residue was treated with sodium bicarbonate solution. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to a solid. Recrystallization from ether-hexane gave 0.8 g, mp 63°-68°, (74% yield) of 4-[6-(2,3-dihydroxyphenyl)hexyloxy]-2-hydroxybenzoic acid ethyl ester.

Workup

  1. customThe solvent was removed on the oil pump
  2. additionthe residue was treated with sodium bicarbonate solution
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated at reduced pressure to a solid
  6. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-1cdb05db2f8648c782e69deb29dcd80f
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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