2-Methoxy-5-ethylphenol

Chemically, wood tar is a complex mixture that contains at least 200 individual compounds, among which the foUowing have been isolated (1) 2-methoxyphenol, 2-methoxy-4-ethylphenol, 5-meth5i-2-methoxyphenol, 2,6-x5ienol, butyric acid, crotonic acid, 1-hydroxy-2-propanone, butyrolactone, 2-methyl-3-hydroxy-4JT-pyran-4-one, 2-methyl-2-propenal, methyl ethyl ketone, methyl isopropyl ketone, methyl furyl ketone, and 2-hydroxy-3-methyl-2-cyclopenten-l-one. 

Benzo[6]furan is cleaved on reduction with excess sodium in liquid ammonia, followed by quenching with ammonium chloride or methanol, to produce 2-ethylphenol (69%). 2-Methyl- and 2-phenyl-benzo[6]furan similarly yield 2-propylphenol (54%) and 2-(2-phenylethyl)phenol (45%) (59JA2795). Similarly, 5-methoxybenzo[6]furan, on reduction with 2 mol of lithium and a limited amount of t- butanol, gives the cleavage product, but by operating with 2 mol each of lithium and f-butanol, 5 -methoxy-2-methylbenzo[6 jfuran supplies the 2,3-dihydro compound. With excess of the alcohol, however, 5-methoxy-2,3,4,7-tetrahydrobenzo[6]furan is secured so that the reduction is stepwise (67JOC2794). 

IUPAC Nomenclature of Phenols Section 9.1C (a) 2-methylphenol (b) 3-bromophenol (c) 4-ethylphenol (ortho, meta, and para in a,b,c respectively is correct also) d) 4-methoxy-2-nitrophenol... 

---