320 BENZYLIC ALDEHYDE. 



in alcohol, particularly in cold. Combines with acids, 

 forming salts which are very difficultly soluble in 

 water and more readily soluble in alcohol. 



Hydrobenzoin, C 14 H 14 2 , is produced from oil of 

 bitter almonds by the action of nascent hydrogen 

 (sodium-amalgam, zinc and hydrochloric acid). Large 

 rhombic plates, which fuse at 132.5, and are volatile 

 without decomposition. Hydrobenzoin conducts itself 

 like a diatomic alcohol, C 14 H 12 (OH) 2 . Diacetylhijdro- 

 benzom, C 14 H 12 (O.C 2 H 3 0) 2 , is produced by the action of 

 acetj r l chloride on hydrobenzoin and by heating stil- 

 bene bromide (p. 283) with silver acetate, ^"eedly 

 crystals, insoluble in water, easily soluble in alcohol. 



Isohydrobenzoin, C 14 H 14 2 . Is formed together with 

 the preceding compound by the action of sodium-amal- 

 gam on a solution of oil of bitter almonds in dilute al- 

 cohol. Long, colorless needles. Fusing point, 119.5. 

 More easily soluble in alcohol than hydrobenzoin. 

 Yields an acetic et her, C 14 H 12 (O.C 2 H 3 0) 2 , with acetyl chlo- 

 ride, that crystallizes in laminae and fuses at 117-118. 



Benzoin, C 14 H 12 2 , is produced by gently heating 

 hydrobenzoin with concentrated nitric acid ; from oil 

 of bitter almonds, which contains prussic acid, by treat- 

 ing it with a concentrated alcoholic solution of caustic 

 potassa, or from that which is free of prussic acid, by 

 mixing it with an alcoholic solution of potassium 

 cyanide, the benzoin separating in crystalline form. 

 Colorless, inodorous prisms. Fusing point, 133-134. 

 Insoluble in water, difficultly soluble in cold alcohol 

 and ether. When treated with alcoholic potassa it 

 yields hydrobenzoin and potassium benzilate. It dis- 

 solves in acetyl chloride, forming hydrochloric acid 

 and the compound, acetylbenzo'in, C 14 H 11 (C 2 H 3 0)0 2 , 

 which crystallizes well and fuses at 75. 



Desoxybenzoin (Toluylen oxide), C 14 H 12 O, is formed 

 by the action of zinc and hydrochloric acid on benzoin 



