TY - JOUR
T1 - Note on the reactivity of some o-(hydroxybenzoyl) benzoic acids towards diazomethane
AU - Bellaart, A.C.
AU - Kooistra, C.
AU - Koningsberger, C.
PY - 1962
Y1 - 1962
N2 - The reactions of CH2N2 (I) and several o-(hydroxyhenzoyl)benzoic acids were investigated both in Et2O and in the presence of MeOH. In all cases the phenolic groups involved appeared to be more or less sluggish in their response. On the other hand, it was noted that nitro groups have an activating influence. Condensation of o-C6H4(CO)2O (Ia) and m-cresol gave 2[4,2-Me(HO)C6H3CO]C6H4CO2H (II) and 2-[2,4-Me(HO)C6H3CO] C6H4CO2H (III). II (6.0 g.) added to excess Et2O-I and the Et2O evapd. when N evolution ceased, gave 5.5 g. Me ester (IV) of II, m. 115-16 Deg (EtOH). Sapon. of IV with N NaOH gave II. Excess Et2O-I added to 4.0 g. II in 70 ml. MeOH and the soln. evapd. (as before) gave 3.5 g. IV, m. 115-16 Deg (EtOH). III (1.5 g.) added to excess Et2O-I and the soln. Reactions between diazomethane and several o-(hydroxybenzoyl)benzoic acids were studied both in purely ethereal solutions as well as in presence of methanol. In all cases the phenolic groups involved appear to be more or less sluggish in their response. On the other hand, it is also noted that nitro groups can exercise an activating influence.
AB - The reactions of CH2N2 (I) and several o-(hydroxyhenzoyl)benzoic acids were investigated both in Et2O and in the presence of MeOH. In all cases the phenolic groups involved appeared to be more or less sluggish in their response. On the other hand, it was noted that nitro groups have an activating influence. Condensation of o-C6H4(CO)2O (Ia) and m-cresol gave 2[4,2-Me(HO)C6H3CO]C6H4CO2H (II) and 2-[2,4-Me(HO)C6H3CO] C6H4CO2H (III). II (6.0 g.) added to excess Et2O-I and the Et2O evapd. when N evolution ceased, gave 5.5 g. Me ester (IV) of II, m. 115-16 Deg (EtOH). Sapon. of IV with N NaOH gave II. Excess Et2O-I added to 4.0 g. II in 70 ml. MeOH and the soln. evapd. (as before) gave 3.5 g. IV, m. 115-16 Deg (EtOH). III (1.5 g.) added to excess Et2O-I and the soln. Reactions between diazomethane and several o-(hydroxybenzoyl)benzoic acids were studied both in purely ethereal solutions as well as in presence of methanol. In all cases the phenolic groups involved appear to be more or less sluggish in their response. On the other hand, it is also noted that nitro groups can exercise an activating influence.
U2 - 10.1002/recl.19620810903
DO - 10.1002/recl.19620810903
M3 - Article
SN - 0165-0513
VL - 81
SP - 739
EP - 747
JO - Recueil des Travaux Chimiques des Pays-Bas
JF - Recueil des Travaux Chimiques des Pays-Bas
IS - 9
ER -