118 



AROMATIC ALCOHOLS AND PHENOLS [56 A-58 C. 



SYNTHETICAL PROCESSES. 



[A.] From phenol [60] through p- 

 hydroxylienzaldehyde [119] by the action 

 of chloroform in the presence of caustic 

 alkali, the o-hydroxy-aldehyde being 

 also formed (Reimer and Tiemann, Ber. 



9, 824; Tiemann and Herzfeld, Ber. 



10, 63), and reduction of the aldehyde 

 with sodium amalgam and dilute sul- 

 phuric acid (Biedermann, Ber. 19, 2374). 



Also from phenol, together with sali- 

 genin, by the action of formic aldehyde 

 in the presence of alkali (see under 

 saligenin [55 ; E]). 



[B.] Parahydrogcyfienzoic acid [Vol. 

 II], by heating its ethyl ester with 

 aqueous ammonia, is converted into p- 

 hydroxybenzamide (Hartmann, Journ. 

 pr. Ch. [2] 16, 50), and the latter on 

 reduction with sodium amalgam in acid 

 solution gives p-hydroxybenzyl alcohol 

 (Hutchinson, Ber. 24, ] 75 ; Auwers 

 and Daecke, Ber. 32, 3373). 



57. Pheiiylethyl Alcohol; Benzyl 

 Carbinol ; l--Phenetliylol. 



C 6 H 5 .CH 2 .CH 2 .OH 



NATURAL SOUECES. 



In small quantity in the steam distil- 

 late from German oil of rose (v. Soden 

 and Rojahn,Ber. 33, 1730 ; 3063 ; Wal- 

 baum and Stephan, Ibid. 2305 ; v. S. 

 and R. Ber. 34, 2803). In dried and in 

 fresh rose petals (Walbaum, Ber. 33, 

 1904; 2299), and to a small extent in 

 Bulgarian oil of rose (v. Soden and 

 Rojahn, Ber. 33, 3065). 



In the aqueous distillate from orange 

 flowers (Hesse and Zeitschel, Journ. 

 pr. Ch. [2] 64, 245). Esters of this 

 alcohol occur in French neroli oil 

 (SchimmePs Ber. Oct. 1902; Ch. 

 Centr. 1902, 2, 1208). 



SYNTHETICAL PEC-CESSES. 



[A.] From phenylacetic and formic 

 acids [Vol. II] by distilling a mixture 

 of the calcium salts (Cannizzaro, Ann. 

 119, 254) which gives a-toluic = phenyl- 

 acetaldehyde. The latter yields the 

 alcohol on reduction with sodium amal- 



gam (Radziszewski, Ber. 9, 373) or, 

 preferably, with zinc and acetic acid 

 (v. Soden and Rojahn, Ber. 33, 1723). 



The generators of a-toluic aldehyde 

 given under phenylethyl mustard oil 

 [170] thus become generators of this 

 alcohol : 



[B.] From benzene or toluene through 

 a-toluic aldehyde (phenylethyl mustard 

 oil [17O ; A]). 



[C.] From styrene [7] through a- 

 toluic aldehyde (170 ; B). 



[D.] From benzoic aldehyde [114], al- 

 cohol [14], and acetic acid [Vol. II] 

 through a-toluic aldehyde (170 ; C). 



[E.] From cinnamic acid [Vol. II] 

 through a-toluic aldehyde (17O ; E). 



[F.] From benzoic and acetic acids 

 [Vol. II] through a-toluic aldehyde 

 (170; F). 



[Gr.] From tartaric or racemic acid 

 [Vol. II] and n-propyl alcohol [15] 

 through a-toluic aldehyde (170 ; D). 



[H.] From cymene [6~J through aceto- 

 phenone and a-toluic aldehyde (170 ; G-). 



58. Methylplieiiyl Carbinol; 

 l^-Fhenethylol ; Styrolyl Alcohol. 



C 6 H 5 .CH(OH).CH 3 



NATUEAL SOUECE. 



Occurs as acetate in Gardenia oil 

 (Parone, Boll. Ch. Farm. 41, 489 ; Ch. 

 Centr. 1902, 2, 704). 



SYNTHETICAL PEOCESSES. 



[A.] From benzene [e] and ethyl al- 

 cohol [14] through ethylbenzene (see 

 under phlorol [64; A]). The latter on 

 bromination at its boiling-point or in 

 presence of strong light gives I 1 -brom- 

 ethylbenzene (see under styrene [7; 

 A]). The latter gives the alcohol ace- 

 tate by interaction with silver acetate 

 (Radziszewski, Ber. 7, 141 ; Berthelot, 

 Zeit. [2] 4, 589). 



[B.] From styrene [7] through i 1 - 

 bromethylbenzene by combination with 

 hydrogen bromide (Schramm, Ber. 26, 

 1710), and then as above. 



[C.] From benz.oic and acetic acids 

 [Vol. II], or from benzene and acetyl 



