The Iodination of Aromatic Compounds. III. Halogenation of Aromatic Ethers in the Presence of Hydrogen Peroxide

1949 ◽  
Vol 2 (4) ◽  
pp. 595
Author(s):  
L Jurd

Aromatic ethers are rapidly iodinated when treated in alcoholic solution with iodine and hydrogen peroxide in the presence of a strong mineral acid. High yields of the mono-iodo-derivatives are obtained with anisole and the 2-naphthyl ethers whilst both mono- and diiodination occur readily with the dimethoxybenzenes. In the absence of a mineral acid the reaction is very slow and only poor yield of the iodo-ethers result. A convenient process is described for the preparation of p-chloro- and p-bromo- anisole, and other chloro- and bromo-ethers, the ether being treated with hydrochloric acid and with potassium bromide and sulphuric acid respectively in the presence of hydrogen peroxide.


1897 ◽  
Vol 21 ◽  
pp. 298-298
Author(s):  
W. R. Lang

In the autumn of 1895 I received from Professor M'Ewen several samples of gastric juice marked “Chalmers' Gastrostomy.” The samples were obtained under most favourable circumstances, being drawn off through an aperture made in the abdomen and stomach of the patient; the juice was almost pure, and nearly free from suspended matter. My analysis was mainly directed towards ascertaining whether or not free hydrochloric acid was a constituent of the fluid, and the following were the reactions I employed:—(1) With methyl violet the sample gave a distinct blue coloration, showing the presence of a mineral acid. Supposing the acidity to be due to lactic acid, this reaction would not take place, as on trying a dilute solution of lactic acid with this reagent no blue colour was produced.(2) On treating an alcoholic solution of phloroglucin and vanillin (1 grm. of the former and ½ grm. of the latter made up with 50 cc.'s rectified spirits) with the gastric juice and evaporating slowly on a water-bath, a red colour was produced. Dilute hydrochloric acid gave the same result; lactic acid none.In the opinion of some authorities the presence of free hydrochloric acid is attributed to the decomposition on evaporation of the chlorides present in the gastric juice by free lactic acid. With a view to ascertain whether this could happen or not, I evaporated solutions of chloride of calcium and lactic acid with both of the above reagents with a negative result.



1950 ◽  
Vol 3 (4) ◽  
pp. 587
Author(s):  
L Jurd

Salicylic acid and p-nitrophenol are almost quantitatively diiodinated when treated in alcoholic solution with iodine, hydrogen peroxide, and sulphuric, nitric, hydrochloric, or phosphoric acid. In glacial acetic acid solution salicylic acid gives good yields of the diiodo compound only in the presence of hydrochloric acid. No appreciable iodination occurs in the presence of sulphuric or nitric acid whilst 3,5-dibromosalicylic acid is formed with hydrobromic acid. Cinnamic acid reacts slowly with iodine, hydrogen peroxide, and sulphuric acid in methanol and ethanol solutions to give the corresponding α-iodo-β-alkoxy-β-phenylpropionic acids. Benzene homologues are readily iodinated in alcoholic solution in the presence of sulphuric or nitric acid although benzene does not react appreciably under similar conditions.



Synlett ◽  
2006 ◽  
Vol 2006 (14) ◽  
pp. 2287-2289 ◽  
Author(s):  
Masayuki Kirihara ◽  
Yoshiro Hirai ◽  
Shiho Ogawa ◽  
Takuya Noguchi ◽  
Kumiko Okubo ◽  
...  


1994 ◽  
Vol 21 (7) ◽  
pp. 565-568 ◽  
Author(s):  
John C. Moore ◽  
Eric W. Wolff ◽  
Henrik B. Clausen ◽  
Claus U. Hammer ◽  
Michel R. Legrand ◽  
...  


2008 ◽  
Vol 38 (22) ◽  
pp. 3894-3902 ◽  
Author(s):  
K. Suresh Kumar Reddy ◽  
N. Narender ◽  
C. N. Rohitha ◽  
S. J. Kulkarni




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