Volume 1

Recent advances in organic chemistry / by Alfred W. Stewart.

  • Alfred Walter Stewart
Date:
1927
Catalogue details

Licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)

Credit: Recent advances in organic chemistry / by Alfred W. Stewart. Source: Wellcome Collection.

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    product containing ecjuimolecular quantities of the two re¬ agents.1 Hydrochloric acid acts upon camphene giving the chloride of an alcohol, isoborneol; whilst a mixture of sulphuric acid and acetic acid produces with camphene the acetate of the same alcohol.2 By the action of nascent nitrous acid upon camphene,3 three compounds are simultaneously formed : camphene nitronitrosite, QloH16(N02)2 • NO ; camphene nitrosite, C10H]6. (N02) . NO ; and camphenylni trite, C10H16.0 . N : 0. When the last com¬ pound is heated with potassium hydroxide solution it yields a ketone, camphenilone, C9H140 ; whilst on reduction it pro¬ duces camphenilan aldehyde, C9H15 . CHO. The same alde¬ hyde is formed from camphene by the action of chromyl chloride and hydrolysis with water.4 5 Oxidation of camphene with alkaline permanganate 0 pro¬ duces an 80 per cent, yield of camphenic acid. M hen nitric acid6 is substituted for permanganate, the first product isolated is camphoic acid, a tribasic acid which on heating loses carbon dioxide and produces apocamphoric acid. This reaction recalls the behaviour of malonic acid ; and the constitution of camphoic acid is therefore assumed to be CH2-CH-COOH I ch3—c—ch3 CH2-CH-COOH Apocamphoric acid. Camphoic acid is also obtained by the oxidation of dihydro - camphene.7 that which is shown below CH, -CH-COOH ■co. CHo—C—CHc -> CH, -C-COOH COOH Camphoic acid. 1 Bouveault, Bull. soc. chim., 1900, (3), 23, 533. 2 Bertram and Wahlbaum, J. pr. Chem., 1894, (2), 49, 8. 3 Jagelki, Ber., 1899, 32, 1501. 4 Bredt and Jagelki, Annalen, 1900, 310, 112. 5 Haworth and King, J., 1912, 101, 1975. 6 Marsh and Gardner, J., 1891, 59, 64 ; 1896, 69, 74. 7 Lipp, Annalen, 1911, 382, 265.
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