Ester: Gamma-Valerolactone

Gamma-Valerolactone

(http://toxicopoeia.com/chemistry/molecules/GVL-sm.png)

Gamma-valerolactone is one of the more common lactones. This compound is a colorless liquid and is used in the perfume and flavor industries because of it's herbal odor.¹ It is also a constituent of crude pyroligneous acid, in dye baths (coupling agent), brake fluid, cutting oils and as a solvent for adhesives, insecticides and lacquers.² Recently, it has been said that gamma-valerolactone is a promising "green" liquid fuel. This compound is derived from furfural:

 (http://www.alanwood.net/pesticides/structures/furfural.gif)


Basic Information
Melting Point: -31°C
Boiling Point: 207-208°C
Water Solubility: Miscible
Density: 1.03 g/mL
Irritant to eyes, respiratory system, and skin


I had a difficult time finding a reaction where gamma-valerolactone was converted to another carboxylic acid derivative. I did find a reaction where gamma-butyrolactone, which is very similar, was converted to alpha-tetralone. I found this on the organic synthesis website provided by Dr. Mullins. In the notes it states that replacing the butyrolactone with 120 grams of gamma-valerolactone in an otherwise identical procedure yields 150–160 grams (79–84%) of 4-methyl-1-tetralone.³ Here is the link so you can see what I'm talking about:
http://orgsyn.org/orgsyn/default.aspformgroup=basenpe_form_group&dataaction=db&dbname=orgsyn

Thanks for reading!


Sources:
1. http://en.wikipedia.org/wiki/Gamma-Valerolactone

2. http://www.erowid.org/chemicals/ghv/ghv_info2.shtml
3.http://orgsyn.org/orgsyn/default.aspformgroup=basenpe_form_group&dataaction=db&dbname=orgsyn