The synthesis of substances allied to epinephrine / by George Barger and H.A.D. Jowett.

  • Barger, George, 1878-1939
Date:
[1905?]
Catalogue details

Licence: Public Domain Mark

Credit: The synthesis of substances allied to epinephrine / by George Barger and H.A.D. Jowett. Source: Wellcome Collection.

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    obtained by the action of dilute hydrochloric acid at 150° on the methylene ether. On attempting to carry out this synthesis with vanillin and proto- catechuic aldehyde, it was found that these substances did not react with magnesium methyl iodide to give the required styrene. Conse¬ quently the synthesis could not be conducted on these lines. Mameli (Gazzetta, 1904, 34, [i], 358) has described a dibromide resulting from the action of bromine water on the styrene, but as this was not identical with the dibromide isolated by us, we repeated his experiments and found that the dibromide described by him is really a bromodihydrin, CH2!02IC6H2Br*CH*0H*CH2Br. We also obtained this compound from the dibromide, CH2!02!CcH3*CHBr*CH0Br, by two distinct methods. Experimental. a-3 : i-Methylenedioxyphenyl-a/3-dibromoet/uine, o-ch2 CHBr CH2Br This substance was obtained from the corresponding styrene, which was prepared from piperonal according to the method described by Klages (Ber., 1903, 36, 3595). In order to eliminate water from the secondary alcohol, it was found preferable to convert it first into the chloride, and then remove the elements of hydrogen chloride with pyridine. 3 :4-Methylenedioxystyrene (20 grams) was dissolved in 20 c.c. of carbon disulphide, and to this a solution of bromine in carbon disul¬ phide (1 gram per c.c.) was gradually added until a faint yellow colour was produced, the liquid being kept cool during the operation. A white, crystalline solid separated, which was collected and washed successively with carbon disulphide and light petroleum. It was recrystallised from carbon disulphide solution by the addition of light petroleum, and thus obtained in white, acicular crystals which melted i at 82—83°. I 04598 gave 04962 AgBr. Br = 522. C9H802Br2 requires Br = 51‘9 percent.