Sulfuric Acid → 2-(2-Chloro-1,1-dimethylethyl)-1-methoxy4-methylbenzene
Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[Cl:15][CH2:16][C:17]([CH3:19])=[CH2:18]>>[Cl:15][CH2:16][C:17]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])([CH3:19])[CH3:18]Komponenten
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a yellow solution of 4-methylanisole (20 g, 183.5 mmol) and 1.7 mL of concentrated sulfuric acid was added 19.17 mL of 3-chloro-2-methylpropene by addition funnel. The reaction became warm and turned dark purple. After 20 minutes, solids began to precipitate. TLC of an aliquot showed some starting anisole left and a new, slightly less polar spot forming. The reaction mixture was stirred overnight and TLC then showed that the reaction was complete. The reaction mixture was poured onto ice and extracted with diethyl ether. The organics were combined, dried over magnesium sulfate, and concentrated in vacuo to leave an oil. The residue was taken up in hexanes, cooled to −78° C., and the solids collected by filtration to give 14 g of 2-(2-chloro-1,1-dimethylethyl)-1-methoxy-4-methylbenzene as an oil upon warming. The filtrate was concentrated in vacuo to give 15.5 g of a 4:1 mixture of product and starting anisole.
Aufarbeitung
- additionby addition funnel
- temperatureThe reaction became warm
- customto precipitate
- waitleft
- customa new, slightly less polar spot forming
- additionThe reaction mixture was poured onto ice
- extractionextracted with diethyl ether
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customto leave an oil
- filtrationthe solids collected by filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-d66977871b8742f19ff228d3f90baa2a
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08741897B2
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