Amyl alcohol from ethyl n-valerate

Fit the central neck of a 1-litre three-necked flask with an efficient double surface condenser and close the two side necks with corks (1). Place 52 g. (59-5 ml.) of ethyl n-valerate (Section 111,104) and 800 ml. of super-diy ethyl alcohol (Section 11,47, 5) (2) in the flask. Add 95 g. of clean sodium in small pieces through one of the apertures at such 

This is an example of the reduction of an ester of a dibasic acid to the corre spending glycol (Bouveault-Blanc reduction)  

Hexamethylene glycol, HO(CH2)gOH. Use 60 g. of sodium, 81 g. of diethyl adipate (Sections 111,99 and III,100) and 600 ml. of super-d ethyl alcohol. All other experimental detaUs, including amounts of water, hydrochloric acid and potassium carbonate, are identical with those for Telramelhylene Glycol. The yield of hexamethylene glycol, b.p. 146-149°/ 7 mm., is 30 g. The glycol may also be isolated by continuous extraction with ether or benzene. 

Both tetramethylene glycol (1 4-butanediol) and hexamethylene glycol (1 6 hexaiiediol) may be prepared more conveniently by copper-chromium oxide reduction (Section VI,6) or, for small quantities, by reduction with lithium aluminium hydride (see Section VI,10). 

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