Formation, during liquefaction of cellulose, of 2,5-dimethyl-1,4-benzenediol via aldol addition and a reduction-oxidation pathway
✍ Scribed by David A. Nelson; Steven D. Landsman; Peter M. Molton
- Book ID
- 102641327
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- English
- Weight
- 293 KB
- Volume
- 128
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Our interest in benzenediol formation was initiated by the isolation and identification of 2,5-dimethyl-1,4\_benzenediol from the liquefaction product of cellulose\*. During that work, 2,5-dimethyl-2,5-cyclohexadiene-1,4-dione (l), 2,3butanedione (biacetyl), and 3-hydroxy-2-butanone (acetoin) were also detected as liquefaction products under aqueous, alkaline conditions. Several alkylbenzenediols have been isolated as alkaline-degradation products of D-xylose and Dglucose'; 1 was observed after treatment of sucrose2 with alkali.
Quite early work had indicated that both 1 and 2,5-dimethyl-1,4-benzenediol (2) could be prepared3 by warming biacetyl (10 g) in dilute caustic solution (200 mL). However, information on the yield was given only for the product from 2,3pentanedione (10% of 2,5-diethyl-2,5-cyclohexadiene-1,4-dione).
Our experience with biacetyl under similar conditions (see Experimental section) suggested that 2 was formed in O.l% when these conditions were applied to biacetyl. However, exposure of acetoin to the same conditions was considerably more successful; yields of 18% of 2 and 0.1% of 1 were obtained. \*Preliminary results were presented before the International Conference on Fundamentals of Thermochemical Biomass Conversion.