Hydrochloric Acid → HCID 9938566, compound

HRID 129355Notes

Reaction equation

HRID 129355 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].[CH2:11]([CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14](Cl)=[O:15])[CH3:12].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH2:11]([CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([O:10][C:3]1[C:2]([I:1])=[CH:7][C:6]([I:8])=[CH:5][C:4]=1[I:9])=[O:15])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 118622,4,6-TriiodophenolHCID 791032-Ethylhexanoyl chloride

Product 1

HCID 9938566HCID 9938566, compoundYield 119.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2,4,6-triiodophenol (20.0 g, 42 mmol), 2-ethylhexanoyl chloride (25 ml, 144 mmol, 3.5 eq.) and 4-dimethylaminopyridine (DMAP; 2 mmol, 250 mg, 0.05 eq.) in 150 ml of pyridine was stirred overnite at room temperature. The solution was poured into 1000 ml of 1N aqueous hydrochloric acid and the aqueous solution was extracted twice with ethyl acetate. The combined organic layers were washed with aqueous hydrochloric acid, water, saturated aqueous sodium chloride and then dried over magnesium sulfate. The ethyl acetate solution was then concentrated under vacuum to give an oil (30 g) which was purified by silica gel chromatography (5% ethyl acetate/hexanes eluent) to give the product. Concentration under high vacuum afforded 21 g (79%) of the desired hexanoate ester as an oil. The product was taken up in hexanes and filtered through a pad of basic alumina. The filtrate was concentrated under high vacuum to give 16.9 g of analytically pure product.

Workup

  1. extractionthe aqueous solution was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed with aqueous hydrochloric acid, water, saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe ethyl acetate solution was then concentrated under vacuum

Sources & evidence

ORD record
ord-a9e540e2a5624194b31608c1f6467c73
Source dataset
uspto-grants-1995_11
Patent number
US05468466

Reaction notes

Loading…