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

  • George Barger
Date:
[1905]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

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

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    amount by the action of phosphorus pentachloride on the dibromide (m. p. 82°) in the attempt to split off the methylene group by the method which Fittig and Remsen used in the preparation of proto- catechuic aldehyde from piperonal (Annalen, 1871, 159, 148). The substance melted at 157—158°, and when mixed with an equal quantity of the dibromohydrin prepared as previously described, the melting point remained unchanged. 0-1355 gave 0-1681 C02 and 0-0308 H20. C = 33-8 ; H = 2-5. 0-1143 „ 0T306 AgBr. Br = 48 6. C9H803Br2 requires C = 33 3 ; H = 25 ; Br = 49-4 per cent. The formation of the dibromohydrin by phosphorus pentachloride is explained by the liberation of bromine which takes place in the first stage of the reaction, and the subsequent formation of the bromohydrin by the action of water on the halogen in the a-position. Attempts were made also to prepare the styrene by distillation of the calcium salts of the corresponding methylenedioxycinnamic acid (compare Tiemann and Will, Ber., 1881, 14, 967). The product obtained was undoubtedly the styrene, as the dibromide was isolated, but the yield was so small (3 per cent.) that this method of preparation had to be abandoned. The necessary physiological experiments in connection with this inquiry were performed by Dr. H. H. Dale, to whom we wish to tender our best thanks. The Wellcome Chemical The Wellcome Physiological Research Laboratories, Research Laboratories, London, E.C. Herne Hill, S.E. It. CLAY AND SONS, LTD., BREAD 6T. HILL, E.O., AND BUNOAY, SUFFOLK.
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