OXYBUTYRIC ACIDS OXYVALERIC ACIDS. 151 



residue dissolved in water, it is converted into ordinary 

 lactic acid. 



3. Oxybutyric Acids. 



1. a-Oxybutyric acid. From monobrombutyric 

 acid by boiling with barium hydroxide. Colorless, stel- 

 late needles or flat prisms ; fusing point, 43-44. When 

 carefully heated it can be sublimed. Deliquescent in 

 the air. 



2. ^-Oxybutyric acid, CH 3 .CH(OH).CH 2 .CO.OH. 

 Is produced by the action of hydrogen (sodium-amal- 

 gam and water) on ethyl ace ty lace tate (p. 82) and by 

 boiling propylene cyanhydrine with caustic potassa. 

 Colorless, syrupy, very deliquescent liquid. 



3. Oxyisobutyric acid, ^ | C(OH).CO.OH. Is 



produced by boiling bromisobutyric acid with barium 

 hydroxide; by the action of cyanhydric and hydro- 

 chloric acids on acetone (acetonic acid) ; by the action of 

 dilute nitric acid on amylene alcohol (hutyllactinic acid) ; 

 by heating methyl oxalate with methyl iodide and 

 zinc, and then treating the product with water 

 (dimethoxalic acid). Colorless prisms, easily soluble in 

 water. Fusing point, 79. Sublimes in long needles 

 even at 50, when carefully heated. "When carefully 

 oxidized with potassium bichromate and dilute sul- 

 phuric acid, it yields acetone, together with carbonic 



and acetic acids. 







4. Oxyvaleric Acids. 



1. Oxyvaleric acid. From bromvaleric acid in a 

 hot aqueous solution by treatment with silver oxide. 

 Its ether is formed when ethyl oxalate is heated with 

 isopropyl iodide and zinc, and the product treated 



