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Treatment of N,N-diacetyl-o-toluidine with N-bromosuccinilllide followed by hydrolysis of the intermediate dibromo compound gave o-acetanlinobenzaldehyde. The reaction was applied successfully to N,N-diacetyl-p-toluidine, N,Ndiacetyl-4-chloro-o-toluidine, 2,4-bis(diacetamino)toluene, and 4-acetosy-N,Ndiacetyl-o-toluidine.Both o-and p-acetaminobenzaldehyde were required for synthetic work in this laboratory. These compoullds have been prepared in the usual way b y the acetylation (6, 7) of o-and p-aminobenzaldehyde. However, the methods described in the literature for the preparation of o-aminobenzaldehyde by the reduction of o-nitrobenzaldehyde with ferrous sulplzate and ammonia (15) and for p-aminobenzaldehyde by the action of sodium polysulphide upon p-nitrotoluene (3) are tedious, and the products must be used immediately in order t o avoid self-condensation.A direct preparation of o-and p-acetaminobenzaldehyde was suggested b y the hydrolysis of N,N-diacetyl-p-toluidine (16) using aqueous sodium carbon-I ate which gave a quantitative yield of p-acetotoluidide, and also by the work of Brown and Newbold (2) who used N-bromosuccinimide to oxidize 4-

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Treatment of 4-hydroxymethyl-7-methoxy-6-methylphthalide with Nbromosuccinimide, followed by hydrolysis of the intermediate bromo-compound, gave deoxygladiolic acid (4-formyl-7-methoxy-6-methylphthalide).The preparation of 3-hydroxymethylopianic acid t from 3-formylopianic acid by catalytic hydrogenation of its monoacetate and subsequent hydrolysis is described. Comparison of the properties of 3-hydroxymethylopianic acid with those of dihydrogladiolic acid shows that the structure of the latter is 3-hydroxymethyl-6-methoxy-5-methylphthalaldehydic acid t rather than Z-hydroxymethyl-3-formyl-6-methoxy-5-methylbenzoic acid as proposed by Raistrick and Ross (Biochem. J., 1952, 635).