Furfural 2-formylfuran

Furans are volatile, fairly stable compounds with pleasant odours. Furan itself is slightly soluble in water. It is readily available, and its commercial importance is mainly due to its role as the precursor of the very widely used solvent tetrahydrofuran (THF). Furan is produced by the gas-phase decarbonylation of furfural (2-formylfuran, furan-2-carboxaldehyde), which in turn is prepared in very large quantities by the action of acids on vegetable residues mainly from the manufacture of porridge oats and cornflakes. Furfural was first prepared in this way as far back as 1831 and its name is derived from furfur which is the latin word for bran in due course, in 1870, the word furan was coined from the same root. 

The separation of aromatic hydrocarbons (as a group) from mixtures with close-boiling paraffins and olefins, such as catalytic reformate or pyrolysis gasoline , is generally effected by extraction with furfural (2-formylfuran), liquid SO2 or other solvents. Benzene, toluene and mixed xylenes are then separated by distillation. 

Furfural 2-Formylfuran, tt-Juraldehyde fur-ftiraJdehyde, ftirfurol, 2-furyloMchyde, 2-furoic aldehyde)... 

On a commercial scale, furan is obtained from 2-formylfuran (furfural, furan-2-carbaldehyde) (see Section 6.2.7) by gas-phase decarbonylation, but in the laboratory, furans can be formed by the cyclodehydration of 1,4-dicarbonyl compounds. Heating in boiling benzene with a trace of /7-toluenesulfonic acid as a catalyst in a Dean-Stark apparatus is often effective (Scheme 6.30a). 

Selective carbonylation of HMF was observed to yield 5-formylfuran-2-acetic acid as the sole carbonylation product the only byproduct was 5-methyl-2-furfural (MF). The activity and selectivity were both found to be strongly influenced by the tppts/Pd ratio the maximum efficiency was observed for tppts/Pd = 6. Replacement of tppts by ligands containing fewer sulfonate groups, e.g., tppds or tppms, led to a dramatic drop in the catalytic activity. Furthermore, it was found that the selective carbonylation of benzyl alcohol to phenylacetic acid also took place in the presence of the catalyst (84). 

Synonyms 2-Furancarboxyaldehyde 2-Furanal-dehyde 2-Formylfuran 2-furfural Fural a-Fural-dehyde... 

Furancarboxaldehyde, 2-furaldehyde, furan-2-carbaldehyde, furfural, furfurol, furanal, 2-formylfuran, pyromucic aldehyde [98-01-1] FEMA 2489... 

Vilsmeier formylation of furans is a good route to formylfurans, though the ready availability of furfural as a starting material, and methods involving lithiated furans (section 15.4.1) are important. Formylation of substituted furans follows the rule that the strong tendency for a-substitution overrides other factors, thus both 2-methylfuran and methyl furan-3-carboxylate give the 5-aldehyde 3-methylfuran gives mainly the 2-aldehyde. ... 

Synonyms 2-Formyl-5-methylfuran 2-Furaldehyde, 5-methyl- 2-Furancarboxaldehyde, 5-methyl- Furfural, 5-methyl- 2-Methyl-5-formylfuran 5-Methyl furaldehyde 5-Methyl-2-furaldehyde 5-Methyl-2-furancarboxaldehyde 5-M ethyIfu rfu ral 5-M ethyl -2-fu rfu ral 5- M ethy If u rf u ral dehyde Empirical C6H6O2... 

---