Methanol → HCID 2750802, compound
Reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]([OH:10])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:19]O>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]([OH:10])[C:7]([O:9][CH3:19])=[O:8])([O-:3])=[O:2]Participants
Procedure
o-Nitromandelic acid (5 g.) and thionyl chloride (50 ml.) were mixed, heated under reflux on a steam bath for 1 hour and cooled, then the excess of thionyl chloride was removed on a rotary evaporator at room temperature. The crude o-nitromandeloyl chloride thus obtained was carefully mixed with methanol (70 ml.), and after the initial vigorous reaction had subsided, the mixture was heated under reflux on a steam bath for 1 hour, cooled, and the solvent evaporated under reduced pressure. The oil thus obtained was chromatographed on silica, and elution with diethyl ether/petroleum ether (b.p. 60°-80° C.), 6:4 by volume yielded methyl o-nitromandelate. The methyl o-nitromandelate thus obtained was reduced by the general process described under (a) above to give the required starting material;
Workup
- temperatureheated
- temperatureunder reflux on a steam bath for 1 hour
- temperaturecooled
- customthe excess of thionyl chloride was removed on a rotary evaporator at room temperature
- customThe crude o-nitromandeloyl chloride thus obtained
- customafter the initial vigorous reaction
- temperaturethe mixture was heated
- temperatureunder reflux on a steam bath for 1 hour
- temperaturecooled
- customthe solvent evaporated under reduced pressure
- customThe oil thus obtained
- customwas chromatographed on silica, and elution with diethyl ether/petroleum ether (b.p. 60°-80° C.), 6:4 by volume
Sources & evidence
- ORD record
- ord-7afff6ef09b14b459c28531ebc2ff923
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04268510
Reaction notes
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