Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C:12](O)=[O:13])[C:5](=[CH:9][C:10]=1[Cl:11])[C:6](O)=[O:7].B.CSC>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[C:5]([CH2:6][OH:7])=[CH:9][C:10]=1[Cl:11]Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A 1.24 g portion of 4,5-dichlorophthalic acid is dissolved in 40 mL anhydrous tetahydrofuran and the solution is cooled to 0° C. To this solution is slowly added 4 mL of borane-methyl sulfide. The reaction flask is first warmed to room temperature, then heated to reflux for 12 hours. The product mixture is cooled to 0° C., then slowly quenched with 50 mL methyl alcohol. Following removal of the solvent, the residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran. The organic layer is washed with 30 mL brine, then dried over magnesium sulfate. Purification by silica gel chromatography (2:1 ethyl acetate/hexane) affords 1.01 g of the desired product as a white solid, m.p. 128°-136° C. MS(Hi res): m/z Calcd for C8H8Cl2O2 205.9901 Found 205.9872
Aufarbeitung
- temperatureThe reaction flask is first warmed to room temperature
- temperatureheated
- temperatureto reflux for 12 hours
- temperatureThe product mixture is cooled to 0° C.
- customslowly quenched with 50 mL methyl alcohol
- customremoval of the solvent
- customthe residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran
- washThe organic layer is washed with 30 mL brine
- dry with materialdried over magnesium sulfate
- customPurification by silica gel chromatography (2:1 ethyl acetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-19d0d4ea4a1f48f8a1d8a0c6bbe7ef17
- Quelldatensatz
- uspto-grants-1996_10
- Patentnummer
- US05561141
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