191J^^ The Condensation of Vanillin 79 



Calculated for CtHi^O^N : C, 68.18; H, 5-73 

 Found: C, 68.53 ; H, 5.79 



S-Methoxy-Jf-hydroxyhenzal-p-anisidine, CHgO.On.CgHoCH:- 

 ]SrC6H4.0CH3, is prepared by boiling 1 gram-molecule of p-anis- 

 idine with 1 gram-molecule vanillin in 10 cc. benzene for six 

 hours. Then after evaporation of the solvent, the product is 

 recrystallized from ligroin. The pale yellow crystals deposit 

 in radiating clusters, are easily solu'ble in most organic solvents 

 and melt at 133.5° (cor.). 



Calculated for CsHiaOsN : C, 70.00; H, 5.88 

 Found : C, 69.96 ; H, 6.09 



3,Jf.-Methyleneoxyhenzal-p-aminohenzoic Acid, CH2 : Oo :- 

 CsHgCH : N'CoH^COoH, is prepared by boiling 1.50 

 gram (one mol) piperonal and 1.37 grams (one mol) p-amino- 

 benzoic acid in 100 cc. toluene for nine hours under a reflux 

 condenser. The time was increased in this case to reduce the 

 amount of a by-product melting at 171 — 3°. The chief product, 

 which crystallized out on cooling, consisted of pale yellow 

 prisms and could be recrystallized from toluene or water. The 

 pure substance melts at 233 — 4°. 



Calculated for G^HnO^N : C, 66.90 ; H, 4.08 

 Found : C, 67.14 ; H, 4.64 



If in the preparation of this compound the boiling was"ii> 

 terrupted after two or three hours, a small amount of a substance 

 melting at 171 — 3° could be readily islated. The amount could 

 be greatly increased 'by employing two molecules of the acid for 

 one of the aldehyde, but no satisfactory analytical figures could 

 be obtained for a product containing two acid residues, in spite 

 of many analyses. 



3,Jf-Methyleneoxyhenzalethyl-p-aminohe7izoate, CHo : Oo :- 

 CgHgCH rNCeH^COgCoHs, is prepared by boiling 1.50 grams 

 j^iperonal and 1.65 grams ethyl-p-aminobenzoate in 10 cc. ben- 

 zene for six hours. The product crystallizes poorly from ben- 

 zene so the latter is evaporated off. Out of ligroin the compound 

 crystallizes readily in long, pale yellow, glistening needles which 

 melt at 109° (cor.). 



