Methanol → 3-Thienylglyoxylic acid
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:12])[C:7]([O:9]CC)=[O:8])=[CH:2]1.[OH-].[Na+].CO>O>[S:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:12])[C:7]([OH:9])=[O:8])=[CH:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of ethyl thien-3-yl-glyoxylate (10 g) and 2 N-sodium hydroxide (50 ml) was added sufficient methanol to produce a homogeneous solution, and the reaction was allowed to stand at room temperature for one hour. The solution was poured into water, extracted with ether, acidified with 2 N-hydrochloric acid and extracted with ether. The combined extracts were dried and evaporated to give an oil which was triturated with benzene-petroleum ether, and the resulting solid filtered and dried (7.5 g; 88%), m.p. 63°, νmax. (Nujol) 3600 and 1702 cm-1 (CO2H), τ (DMSO-d6) values include 1.29, 2.21, 2.38 (thien-3-yl protons).