170 D-171.] 



PHENYLETHYL ISOTHIOCYANATE 



261 



Or phenylglycidic acid (ester) by the 

 action of sodium amalgam gives phenyl- 

 a-lactic acid (Plochl, Ber. 16, 2823), and 

 the latter yields a-toluic aldehyde on 

 heating per se at 130 or with dilute 

 sulphuric acid at 200 (Erlenmeyer, 

 Ber. 13, 304). Subsequent steps as 

 above under A. 



Or from benzoic aldehyde and hydro- 

 gen cyanide [172] through the nitrile of 

 mandelic acid (see under benzyl mustard 

 oil [169; B]). This nitrile, according 

 to Fileti (Schiff, Ber. 12, 297; 1700), 

 can be reduced to phenylethylamine. 



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

 and carbon disulphide [16 0]. Cinnamic 

 acid can be converted into phenyl-a- 

 chlorlactic acid by combination with 

 hypochlorous acid (Glaser, Ann. 147, 

 79 ; Erlenmeyer and Lipp, Ann. 219, 

 185). Phenyl-a-chlorlactic acid on 

 treatment with cold alcoholic potash 

 gives /3-phenyloxy aery lie acid (Glaser, 

 loo. cit. 98), which can be treated as 

 above under D. Or the phenyl-a- 

 chlorlactic acid yields a-toluic aldehyde 

 directly on distillation with sodium 

 carbonate solution (Forrer, Ber. 17, 

 982). 



Or cinnamic acid can be combined 

 with bromine, and the phenyldibrom- 

 propionic acid converted by boiling 

 with water into phenyl-a-bromlactic 

 acid (Glaser, loc. cit. 84 ; Erlenmeyer, 

 Ber. 13, 310). The latter gives /3- 

 phenyloxyacrylic acid on treatment with 

 alkali (Glaser, loc. cit. 98). 



Or cinnamic acid on combination 

 with a hypobromite and treatment of the 

 product with alkali gives a-oxyphenyl- 

 propionic lac tone, which, on heating in 

 a partial vacuum or with water, yields 

 a-toluic aldehyde (H. Erdmann, Eng. 

 Pat. 8248, April, 1899; Journ. Soc. 

 Ch. Ind. 19, 273). 



Sodium cinnamate on treatment with 

 iodine chlorhydride gives phenyliodhydr- 

 acrylic = a-iodo-/3-phenyl-/3-hydroxy- 

 propionic acid, and this on heating with 

 water yields a-toluic aldehyde (Erlen- 

 meyer and Rosenhek, Ber. 19, 2464 ; 

 Erlenmeyer, Ann. 289, 276). 



Or from cinnamic acid through 

 phenylgly eerie acid (see under benzoic 

 aldehyde [114 ; E]). The latter gives 



phenyl-/3-chlorlactic acid or the corre- 

 sponding bromo-acid by treatment with 

 hydrochloric or hydrobromic acid(Lesch- 

 horn, Ann. 271, 153 ; Lipp, Ber. 16, 

 1 290). The phenyl-/3-chlor- (or bromo-) 

 acid yields a-toluic aldehyde on distilla- 

 tion with dilute alkali (Erlenmeyer and 

 Lipp, Ann. 219, 182). Phenylglyceric 

 acid gives a-toluic aldehyde directly on 

 heating to 160 (Lipp, Ber. 16, 1288). 



[F.] From benzoic and acetic acids 

 [Vol. II] through acetophenone (see 

 under benzoic aldehyde [114; A and 

 G]), dypnone, and ethylbenzene (see 

 under phlorol [64 ; K]), and then as 

 above under A. 



[G-.] Cymene [6] can be conveited 

 into acetophenone through cumic acid 

 and isopropylbenzene = cumene (see 

 under benzoic aldehyde [114; K]). 



[H.] From plienylacetic (a-tohnc) and 

 formic acids [Vol. II] by distilling 

 a mixture of the calcium salts (Canniz- 

 zaro, Ann. 119, 254), and treating the 

 a-toluic aldehyde thus formed as above 

 under A. 



[I.] ft-Pkenylpropionio acid [Vol. II] 

 is converted into its amide (Hofmann, 

 Ber. 18, 2740), and the latter into 

 co -phenylethylamine by the action of 

 bromine in presence of potassium hydr- 

 oxide (Ibid. ; also Hoogewerf and Van 

 Dorp, Rec. Tr. Ch. 5, 254). 



[J.] Phevylalanine [Vol. II] gives 

 to-phenylethylamine on rapid heating 

 (Erlenmeyer and Lipp, Ann. 219, 202 : 

 see also Schulze and Barbieri, Journ. 

 pr. Ch. [2] 27, 346; Ber. 14, 1788; 

 16, 1713). 



171. Farahydroxybenzyl Isothio- 



cyauate, Tliiocarbimide, or 



Mustard Oil. 



CH, . NCS 



HO 



NATURAL SOURCE. 



Occurs in the oil of white mustard 

 from the seeds of Sinapis alba. The 

 glucoside contained in the seeds is sin- 



