ON ISOMERIC CRE80LS AND THEIR DERIVATIVES. 113 



OH OH 



I I ■*■ I II S 



CH 



1 .CH HC s 



HC^ I ^CH 



H (CH(^ 



Phenol. Paracresol. 



CH 



So far as the action of nitric acid is concerned, it may be said that sucli is 

 really the case ; but the behaviour with bromine does not appear to be in har- 

 mony with the " law." Thus paracresol is readily converted into nitropara- 

 creso] ; and this compound evidently has the nitro-group in the ortho-position, 

 since it is identical with the orthonitroparacresol recently obtained by 

 "Wagner from orthonitroparatoluidin. By the further action of nitric acid, 

 orthonitroparacresol is converted into a dinitroparacresol, which, there is 

 every reason to believe, has both nitro-groups in the ortho-positions ; it is 

 not possible, however, to introduce a greater number of nitro-groups into 

 paracresol. Similarly, by the action of bromine and iodine on orthonitro- 

 paracresol, monobromo- and moniorfo-nitroparacresol only can be obtained. The 

 behaviour of paracresol with bromine has not yet been examined; but the action 

 of bromine on potassium paracresolorthosulphonate, C^ H^ (CH3) OH SO^ K, has 

 been studied. From this compound, in the first instance, the corresponding 

 bromoparacresolorthosulphonate, C,, H.^ Br (CH3) OH S03K,is produced; but on 

 further treatment with bromine this is converted into ^nbromoparacresol, and 

 hitherto no intermediate product has been detected. The tribromoparacresol 

 thus formed has not yet been sufficiently examined to enable an opinion as to 

 its nature to be pronounced ; it is a remarkably unstable compound, being de- 

 composed and deprived of a portion of its bromine by mere dissolution in alco- 

 hol. This behaviour is certainly remarkable, and may serve on investigation 

 to throw light on the formation of a tri-derivative from paracresol, which at 

 present we are inclined to regard as abnormal. Potassium bromoparacresol- 

 orthosulphonate is readily converted by the action of nitric acid into a bromo- 

 nitrocresol identical with that obtained by treating orthonitroparacresol with 

 bromine. 



Thymol derivatives. — Thymol being formed from phenol by the displace- 

 ment of an atom of hydrogen in the ortho-position by the group propyl, and 

 a second atom in the meta-position by the group methyl, it should " theore- 

 tically " furnish only cZi-derivatives, thus : — 



OH OH 



EC ^*T^^ CH HC ^1 ^ C (CaHf) 



I 



! 



! I 11 i 



HC j CH (CH3)C^ I ^CH 



H H 



Phenol. Thymol. 



1875. 



