Hydrochloric Acid → Methyl 3-hydroxy-4-(methylthio)benzoate
Reaction equation
Cl.N[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[S:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7].N([O-])=[O:16].[Na+]>O>[OH:16][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[S:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of concentrated hydrochloric acid (3.2 mL) in water (3.6 mL) at from 0° C. to 5° C. is treated with methyl 3-amino-4-(methylthio)benzoate (1.97 g; that is prepared as described in Reference Example 52), followed by a solution of sodium nitrite (0.82 g) in water (2 mL), at such a rate that the temperature remains from 0° C. to 5° C. The mixture is then allowed to warm to room temperature and it is stirred for a further period of 1 hour. The reaction mixture is treated with water (30 mL) and then heated to 55°-60° C., until the evolution of nitrogen ceased (4 hours). The mixture is extracted with dichloromethane (2×100 mL) and the combined organic extracts are dried and concentrated. The resulting brown oil is subjected to flash chromatography, eluting with a mixture of diethyl ether and pentane (1:4 v/v), to give methyl 3-hydroxy-4-(methylthio)benzoate (0.6 g) in the form of a yellow solid.
Workup
- customthat is prepared
- customremains from 0° C. to 5° C
- temperatureheated to 55°-60° C., until the evolution of nitrogen
- custom(4 hours)
- extractionThe mixture is extracted with dichloromethane (2×100 mL)
- customthe combined organic extracts are dried
- concentrationconcentrated
- washeluting with a mixture of diethyl ether and pentane (1:4 v/v)
Sources & evidence
- ORD record
- ord-a113f2f4a8ee4a008e2d6b96ecdac913
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05698711
Reaction notes
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