Sulfuric Acid → 4-(5-Chloropyridin-2-yl)cyclohex-3-enecarboxylic acid
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=2)(O)[CH2:8][CH2:7]1)=[O:5])C.S(=O)(=O)(O)O>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH:8]=2)=[N:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 4-(5-chloropyridin-2-yl)-4-hydroxycyclohexanecarboxylic acid ethyl ester (1.6 g) and sulfuric acid (5 ml) is heated at 60° C. for 15 minutes. After addition of water (0.4 ml) the mixture is again heated at 60° C. for 20 minutes. The cooled reaction mixture was diluted with water and washed with dichloromethane. The aqueous phase was adjusted to pH 7 with sodium bicarbonate solution and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The product with the molecular weight of 237.69 (C12H12ClNO2); MS (ESI): 238 (M+H+) was obtained in this way.