y -benzoylchloride, a number of their substitution products, and oxalylbromide were con- 
-densed. with various aromatic aldehydes, Os benzaldehyde, anisaldehyde, terephthalic 
. aldehyde, acetylvanillin, piperonal, methylsalicylaldehyde, methylvanillin, cinnamic 
si ine aldehyde and furfural. Addition products were formed from one molecule of acid 
: __— haloid and one molecule—in the case of oxalylbromide 2 molecules—of aldehyde, of 
the general formule RCHXO-CO-R’ and R-CHXO-CO-COOCHXR’ (X = halogen). 
The correctness of these formulz is proved by the reaction product of benzoyl- 
= bromide and benzaldehyde chosen as an example. In consideration of the comparative — 
s, instability of this compound, and that in ‘several cases it behaves as a mixture of 
: ae yee and halide, one or other of the following. formulz may be assigned to it. 
es ae ee OX 
eee CoHsCHC > apa CoH. ClOHDBrCOCsHs CsH;CHBrOCOCHs. 
Ree. MEAT ny | QTR) ok fea he 
fe would | be such an unstable compound that it could not be isolated. On the contrary, 
the third formula which represents the compound as an ether — phenylbromomethyl 
~ benzoate, should be the correct one. If Silver benzoate be ‘caused to react with the oe 
be compound, benzylidene benzoate is formed. \ 
ae “ _ CcHsCHBrOCOC.H; 4 CHsCOOAg = —: AgBr i CH CH(OCOCcH)s. 
ee: With water all halide-aldehyde compounds decompose more or less rapidly into 
Sales aldehyde, the organic acid and the halogen acid. 
~ CH;CHBrO- COCH, => ColLEOH, = C,HsCHO +- HBr ae CsHsCOOC3Hs. 
_ benzaldehyde and benzoylbromide. 
a ee , | 
ee The first formula, given in “Beilstein” wie the 4 linked-ring, is improbable, the 
a ~ second with an. hydroxy! group and a halogen attached to the same carbon atom oa 
| PAaibonia dissolved in dry ether splits the addition-compound at once into benz- 
& as benzaldehyde, and ammonium bromide. Aniline dissolved in dry ether, on the — 
_ contrary, reacts quite differently with phenylbromomethy! benzoate. Phenylbromo- — 
- methyl aniline and benzoic acid are produccds without in the least any splitting ine 
From e: 
i ity appears that the reaction is a aR “one. Benzoylivouiiene ; 
ot Bes ae 
ee MS Sa ee a at te 
Cold absolute alcohol reacts very slowly with the phenylbromomethyl bensoatee 4 
~ and forms i in the course of 24 hours benzaldehyde, Ee Soro acid, and ethyl benzoate. mil: 
q . 3 ee " . CsHsCHBrOCOC.Hs ~ CcHsNA, = = CoHs CHBrNHCcHs -- C;H;COOH. 
3 ‘Accordingly the addition- ae behave on the one hand as if they were 
oie _mereiy a. mixture of aldehyde and halide, on the other, however, they give quite 
BLS ee Achaia, reactions, which mark ‘hem as chemical pomneuecs (esters). 
an % In a ede on the action of ammonia on acetaldehyde O. “Aschan 5) publishes his 
stitution of aldehyde-ammonia. Aschan showed that the melting point stated in books 
mew way by means of concentrated aqueous ammonia, melts at 96 to 98°. From the 
oe ie escopic molecular-weight determination in aqueous solution (molecular weight found 
a 
1) Berl. Berichte 7 (1384), 911; 42 (1909), 30060; 46 (1913), 1425. — 2) Ten, Americ. chem Soc. 40 (1918), 
— ’) aba of Sore Vetenskaps-Societetens Forhandling gar 57 (1914/15). Afi. A, No. 14. 
/ 
‘ 
€3 _ observations, which considerably enlarge our knowledge of the formation and con- 
4! —70 to 80° —is too low, and that pure aldehyde-ammonia, which he obtained in a 
