— 139 - 



on this subject has been published 1 ) which enables us to complete our 

 previous statements. For the purpose of preparing the aldehyde from 

 15 to 20 kilos green hornbeam leaves are ground up finely. The paste mixed 

 with its own volume of water is distilled with steam, the total quantity 

 of distillate recovered being 7 litres. The distillate is then diluted with 

 an alcoholic solution of 7 grams m-nitrobenzohydrazide, which must have 

 been previously freed from m-nitrodibenzohydrazide by recrystallisation 

 from alcohol. As we have already stated in our previous abstract, the 

 hexylenic-aldehyde-m-nitrobenzohydrazide obtained by this method has 

 m. p. 166 to 167°, which is also the m. p. of the product prepared from 

 the pure aldehyde. The ^-nitrophenylhydrazone melts at 137°. 



The m. p. of hexylenic aldehyde benzohydrazone lies between 112 and 

 113° (recrystallised from a mixture of benzene and ligroin). The aldehyde is 

 recoverable from the hydrazone by boiling with dilute sulphuric acid. It boils 

 at 47 to 48° (17 mm.) but apparently it cannot be distilled without showing 

 indications of decomposition or polymerisation. It constitutes a colourless 

 oil with a peculiar characteristic odour: d^^ 0,8470, n D17 , 9 o 1,44602. The 

 «,/#-hexylenic aldehyde was oxidised by Delepine's method, 2,2 g. of the 

 aldehyde being dissolved in 50 cc. alcohol and diluted with a solution of 6 g. 

 silver nitrate in 30 cc. water. A solution (say, seminormal) of 2,2 g. sodium 

 hydroxide is next added to the mixture, slowly and under constant stirring, 

 in the course of an hour, and finally the mixture is shaken up in the 

 machine for 3 hours. The «,/?-hexylenic acid separates out from the liquid 

 which has been filtered off from the silver; it is oily at first, but when 

 cooled with ice it immediately congeals into a colourless crystalline mass. 

 After purification from light petroleum it has m. p. 32 to 33°. By the 

 addition of bromine it yields «,/?-dibromo caproic acid (m. p. 71 to 72°). 



The presence of hexylenic aldehyde in the following plants was 

 demonstrated: Grape vine (Vitis vinifera), edible chestnut (Castanea vesca), 

 common oak (Quercus scssili flora), brake, elder (Sambucus racemosa), common 

 hazel (Corylus avellana), horse chestnut (Msculus Hippocastanum), birch 

 (Betula alba), common beech (Fagus silvatica), clover (Trifolum repens). 

 raspberry (Rubus Idceus), willow, walnut (Juglans regia), Norway maple 

 (Acer platanoides), poplar, acacia (Robinia Pseudacacia) and ash. 



The precipitates which have been obtained with m-nitrobenzohydrazide 

 ■by Reinke and Braumuller 2 ) from the distillates of certain other plants 

 likewise, in some cases, consist chiefly of condensation-products of 

 «,/2-hexylenic aldehyde. Hence the following plants should be added to 

 those which have been examined by Curtius and Franzen: Syringa vidgaris, 

 Mgopodium Podagraria, Polygonum sachalinense, Ulmus campestris, Sambucus 

 nigra. Alnus incana. and Vinca minor. 



x ) Curtius and Franzen, Liebigs Anhalen 890 (1912), 89. 

 2 ) Com p. Report April 1911, 160. 



