148 Report of Schimmel § Co. 1922. 



in light petroleum. When trying to reduce it to furyl camphor by catalytic reduction 

 according to Sabatier and Senderens in presence of nickel, it was completely reduced 

 to tetrahydrofurylcamphor, b. p. 166° (14 mm.). 



Following the process worked out by Haller and Bauer 1 ) the author prepared, via 

 the organomagnesium compounds: — phenylfurylcamphor CioHisO-CHCCbHs^CJIbO, 

 m. p. 1 1 4°, benzylf urylcamphor, C 10 Hi 5 O • CH(C 7 H?) • C 4 H 3 (viscid oil) ; p-tolylf urylcamphor, 

 C 10 H 15 OCH(C 6 H4-CH 3 )C4H3O, b.p. 234° (17 mm.); ^-anisylfurylcamphor, C 10 H 15 O-CH 

 (C 6 H 4 OCH3)-C 4 H 3 0, b.p. 255° (17 mm.). 



In a later communication, the author publishes the molecular refractions and the 

 specific rotations of the above-mentioned compounds, which agree with the constants 

 found formerly by Haller and Miiller 2 ) with the condensation-products from camphor 

 and aldehydes. Furalcamphor shows a strong exaltation of the molecular refraction, 

 the specific rotation, and the molecular dispersion, which is caused by the double bond 

 linked to the furane nucleus and which disappears on reduction. 



In connection with earlier work done on mono- and dialkyl derivatives of camphor 3 ), 

 A. Haller and P. Ramart 4 ) communicate that the amide of dimethylcampholic acid shows 

 the m. p. 81 to 82° and not, as stated before 5 ), 72 to 73°. On reducing this amide with 

 sodium and absolute alcohol, the authors obtained, on rectification, the nitrile of dimethyl- 



/CH(CH 3 ) 2 

 campholic acid C 8 H 14 <^ (b.p. 131 to 133° [14 mm.], 245 to 247° [ord. press.]). 



On heating with sulphuric acid to 85 to 100° the nitrile again passes over into the 

 original amide (m. p. 81 to 82°). When the nitrile was reduced with sodium and absolute 

 alcohol, dimethylcampholamine (b.p. 123 to 124° at 20 mm.; [«] D25 o +30.1°) resulted in 

 quantitative yield. By reducing the phenyl ester of dimethylcampholic acid (b.p. 190 to 

 195° at 30 mm.) — not though with the ethyl ester — with sodium and absolute alcohol, the 

 authors obtained dimethylcampholic alcohol (b. p. 139 to 140° at 20 mm.; [a] D24 o + 32°). 



As to the preparation of camphor from pinene hydrochloride see p. 137 of this Report. 



Epicamplior. — \n continuation of the paper by J. Bredt and W. H. Perkin jun. 6 ) 

 which dealt with the preparation and the properties of epicamphor, Perkin jun. and 

 A. F. Titley 7 ) have prepared some derivatives of /-epicamphor which they compare with 

 the analogous bodies obtained from the isomeric ^-camphor 8 ). 



When Z-epicamphor is treated with sodium and isoamyl formate in presence of 

 ether, hydroxymethylene-Z-epicamphor is formed (m. p. 89°, turning but slowly yellow 

 and viscous; semicarbazone, m. p. 197°) to which the authors assign, in analogy to 

 the constitution 9 ) assumed for hydroxymethylene-d-camphor, the formula (I) 



CO CH O 



. i i ; 



C(CH 3 ) 2 C-OH 



I II 



CH 2 C CH 



CH 3 CH3 



(I) Hydroxymethylene-epicamphor. (II) Lactone of hydroxyketodihydroepicampholenjc acid 



(tautomeric formula). 



!) Compt.rend. 142 (1906), 971; 146 (1908), 717. — 2 ) Ibidem 128 (1899), 1370. — 8 ) Cf. Report 1919, 160. 



— ±) Cotnpt. rend. 173 (1921), 682. — 5 ) Report 1919, 161. — 8 ) Cf. Report April 1914, 140. — 7 ) Journ. 

 diem. Soc. 119 (1921), 1089. — 8 ) Liebig's Ann. 281 (1894), 314; 356 (1907), 251. — Berl. Ber. 30 (1897), 243. 



— 9 ) Journ. chem. Soc. 95 (1909), 171. 



