Methanol → Benzoic acid, 3-amino-, methyl ester

Participants

Reaction Steps

To a chilled solution of methanol (100) was added thionyl chloride (21.25 ml, 0.29 mol). The solution was stirred for a further 30 minutes after which time m-aminobenzoic acid (10 g, 73 mmol) was added. The reaction was allowed to proceed overnight at room temperature and the solvents were then removed under reduced pressure. The product was obtained on tituration of the residue with diethyl ether. Yield 12.2 g (89%), m.p. 216°-218° C. The product was judged homogeneous by tlc in chloroform/methanol (4:1) (Rf 0.688) or chloroform/methanol (1:1) (Rf 0.597). (Found: C, 50.16; H, 5.27; N, 7.29. C8H10O2N1Cl1 requires C, 50.26; H, 5.23; N, 7.33%).

Provenance & Evidence