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温度

0 °C

A solution of chlorosulphonyl isocyanate (5.35 ml.) in dichloromethane (3 ml.) was added over 45 minutes to a stirred suspension of 3-methoxy-4-methylbenzoic acid (9.97 g.) in dichloromethane (18 ml.) at reflux under an atmosphere of nitrogen. The resulting bright-red homogeneous solution was heated under reflux for 45 minutes, chilled in an ice-bath, and treated dropwise with N,N-dimethylformamide (9.5 ml.), over 15 minutes. After stirring for 30 minutes at 0° C., the orange solution was poured onto ice. The organic layer was separated, washed with water (5×20 ml.), dried (MgSO4) and evaporated. The residue was purified by preparative HPLC (SiO2, 10:90 v/v hexane: toluene) to give 3-methoxy-4-methylbenzonitrile (5.28 g., 60%) as a white solid, m.p. 51°-52.5° C.

1. temperatureat reflux under an atmosphere of nitrogen
2. temperatureThe resulting bright-red homogeneous solution was heated
3. temperatureunder reflux for 45 minutes
4. temperaturechilled in an ice-bath
5. additionthe orange solution was poured onto ice
6. customThe organic layer was separated
7. washwashed with water (5×20 ml.)
8. dry with materialdried (MgSO4)
9. customevaporated
10. customThe residue was purified by preparative HPLC (SiO2, 10:90 v/v hexane: toluene)