반응 #81775

반응 방정식

malonate

2,4,6-triiodophenol

potassium carbonate

2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diethyl ester

→

Diisopropyl 2-(2,4,6-Triiodophenoxy)-1,3-propanedioate

용매

—

hexanes

dimethylformamide

ether

ethyl acetate

—

hexanes

반응 조건

후처리

1. 1
   추출in the aqueous extraction, 2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diisopropyl ester

실험 절차

A stirred solution of 18.8 g (0.1 mol) of diisopropyl malonate in 100 ml carbon tetrachloride was cooled in an ice bath and 15.8 g (0.1 mol) bromine was added dropwise over a 90 minute period. The ice bath was removed and the reaction stirred at room temperature for 20 hours. The reaction solution was concentrated in vacuo and the resulting residue distilled to yield 16.1 g (76%) of the bromomalonate I [H. P. Gallus and A. K. Macbeth, J. Chem. Soc., 1937, 1810-12] as a dear colorless liquid; Bp 51°-2° C./0.1 mm Hg. CI/MS: MH+ 26. 1H-NMR (300 MHZ) spectral data was consistent with the desired structure. Using the same procedure as for 2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diethyl ester, but substituting methylene chloride for ethyl acetate in the aqueous extraction, 2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diisopropyl ester was prepared from 8.6 g (0.03 mol) of malonate I, 107 g (0.03 mol) of 2,4,6-triiodophenol, 4.5 g (0.03 mol) of milled anhydrous potassium carbonate and 30 ml of dimethylformamide in 69% yield as a tan oil; bp >65° C./0.65 mm Hg after chromatography (hexanes to 5% ether in hexanes).

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