— 17 - 



alkaline solution of the phenol acquires very rapidly a dark red colour. 

 Its odour is comparatively faint, and distantly reminds of creosote. 

 The phenol dissolves readily in water. 



Some of the properties mentioned above allowed the conclusion 

 to be drawn that this body is a derivative of pyrocatechol. The 

 analysis shows that to this phenol belongs the gross formula C 9 H 10 O 2 : 

 I. 0,1560 g. substance: 0,4101 g. C0 2 , 0,0978 g. H 2 

 II. 0,1737 g. „ 0,4593 g. „ 0,1121 g. „ 



III. 0,1665 g. „ 0,4400 g. „ 0,1046 g. 



Found : Calculated for C 9 H 10 2 : 



1. 11. 111. 



c 71,69% 72,19% 72,07% 72,00% 



H 6,97 o/ 7 ,i 7 o/ 7,00%, 6,67% 



The methoxyl-determination according to Zeis el showed that the 

 molecule contained no. methoxyl-group. The benzoyl compound pro- 

 duced by Schotten-Baumann's method forms coarse, faintly reddish 

 prisms of the m. p. 71 to 7 2 . According to the combustion it is 

 a dibenzoyl compound. 



I. 0,1714 g. substance: 0,4836 g. C0 2 , 0,0792 g. H 2 

 II. 0,1680 g. „ 0,4750 g. „ 0,0804 g. „ 



Found : Calculated for C 23 H 18 4 : 



1. 11. 



c 76,95% 77,o8 % 77,10% 



H 5,13% 5,3i% 5,03% 



The dibenzoyl compound no longer reacted with ferric chloride. 

 A diacetyl compound was obtained as a colourless oil of the b. p. 15 7 

 (7 mm. pressure), 299 (atmospheric pressure). Although it showed 

 an inclination to solidify, the quantity was so minute that it was 

 impossible to isolate a solid substance. On methylating with di- 

 methyl sulphate, the phenol was converted ineugenol methyl ether. 

 The reaction-product driven over with steam had the following con- 

 stants: b. p. 108 to 109 (4 mm. pressure), 248 to 249 (ordinary 

 pressure), n D20° I ,537 I 5- The fact that it was here indeed a question 

 of eugenol methyl ether was proved both by oxidation with potassium 

 permanganate, and by bromination. In the former case there re- 

 sulted dimethylprotocatechuic or veratric acid of the m. p. 179 to 180 , 

 in the latter, the characteristic tribromide of the m. p. 79 to 8o° which 

 solidifies when stirred with alcohol. A mixture of this compound with 

 one produced from pure eugenol methyl ether, had the same melting 

 point. Oxidation of the diacetyl compound with 2 per cent, per- 

 manganate solution unfortunately had not the desired effect. 



The conversion of the divalent phenol to eugenol methyl ether 

 supplied the proof that the body is allyl pyrocatechol, i. e. an 



2 



