124 REPORTS ON THE STATE OF SCIENCE.—1912. 
The Study of Hydro-aromatic Substances.—Report of the Com- 
mittee, consisting of Professor A. W. CrossuEy (Secretary), 
Professor W. H. Perkin, Dr. M. O. Forster, and Dr. H. R. 
Le SUEuR. 
1. The behaviour of c-acetyldimethyl- and c-acetyltrimethyldihydro- 
resorcins towards hydroxylamine and phenylhydrazine.—It has been 
pointed out? that trimethyldihydroresorcin does not behave towards 
many reagents in a similar manner to dimethyldihydroresorcin, for it 
exhibits tautomeric forms and also its molecule is not symmetrical. In 
order to clear up several points of interest the c-acetyl derivatives of 
these two dihydroresorcins are being investigated. 
C-acetyldimethyldihydroresorcin behaves as a monobasic acid and 
may be represented by one or other of the following formule, probably 
C Me, C Me, 
HO.C co Oc co 
4 “ 
C 
| lI 
Me.CO Me.C.OH 
the second. When acted on by hydroxylamine it gives an acid oxime 
(I.), an isoxazole (II.), and an oxime of the isoxazole (III.), and with 
C Me, C Me, C Mey 
H.C CH, H.C CH, H.C CH, 
OC C=N.OH OC C=N HO.N=C C=N 
em A 
Me.C—OH Me.C Me.C 
L. II. II. 
phenylhydrazine it behaves in a similar manner giving an acid phenyl- 
hydrazone, a phenylpyrazole, and a phenylhydrazone of the phenyl- 
pyrazole. 
The behaviour of c-acetyltrimethyldihydroresorcin towards hydroxy]- 
amine has not been investigated owing to the fact that the isoxazole is 
a liquid or very low melting solid; but with phenylhydrazine it gives an 
acid phenylhydrazone and a phenylpyrazole, though all attempts to 
prepare a phenylhydrazone of the phenylpyrazole have so far failed. 
It is presumed that c-acetyltrimethyldihydroresorcin is similarly con- 
stituted to the corresponding derivative of dimethyldihydroresorcin, 
but the results will be discussed at length in another publication. 
2. The action of phosphorus pentabromide on dimethyldihydro- 
resorcin.—In 1903 it was shown? that phosphorus pentabromide acts 
on dimethyldihydroresorcin to give several bromodimethylcyclohexa- 
nones and also certain bromoxylenols. One of the latter substances 
(melting-point 96-97°) was thought to be a derivative of 1 :2-xylenol-3, 
and this has now been definitely shown by synthesis which proves it 
to be 4: 5-dibromo-1: 2-xylenol-3. The formation of this substance 
1 J.C.S., 1911, 99, 1101. 2 [bid., 88, 110. 
