2,3-Dimethylbenzaldehyde

Clear Colorless Oil

Preparation of 2.3-dimethylbenzaldehydeDIBAL-H Toluene 2, 3-Dimethylbenzonitrile (50.0 g, 381 mmol) was dissolved in 100 mL toluene. The solution was cooled in an ice bath to 5 Was added under nitrogen atmosphere in a reaction flask26.4Magnesium turnings (1.1 mol)And 160 ml of tetrahydrofuran, 18.5 g of 2, 3-dimethylbromobenzene (0.1 mol) was added dropwise with stirring at room temperature, and100 ml of tetrahydrofuran, Triggering reaction, Then, 166.5 g of the solution was added dropwise2, 3-dimethylbromobenzene (0.9 mol) and 1000 ml of tetrahydrofuran, Upon completion of the addition, The reaction was refluxed for 1 hour.The resulting Grignard reagent was cooled in an ice bath, 73 g of N, N-dimethylformamide (1.0 mol) and 300 ml of tetrahydrofuran were added dropwiseFuran mixture, Control reaction temperature is not higher than 20 degrees, After completion of the addition, the reaction was continued at room temperature for 2 hours.After completion of the reactionPlus 1000 ml of saturated ammonium chloride solution for hydrolysis 1 hour, The organic phase was then separated by standing, and the aqueous phase was extracted with ethyl acetateThe organic phase was washed with 500 mL of saturated brine and allowed to stand for separation. The organic phase was stirred and dried with 50 g of anhydrous sodium sulfateThe filtrate was concentrated to dryness under reduced pressure to give 2, 3-dimethylbenzaldehyde in a yield of 96percent and a purity of 96.2percent.Under nitrogen protection, 24 g of magnesium turnings (1 mol) and 160 ml of tetrahydrofuran were added to a reaction flask and stirred at room temperature18.5 g was added dropwise2, 3-dimethyliodobenzene (0.1 mol) and100 ml of tetrahydrofuran, Triggering reaction, Then, 166.5 g of 2, 3-dimethyliodobenzene (0.9 mol) was added dropwise1000 ml of tetrahydrofuran mixture, drop finished, reflux reaction 1hour. The resulting Grignard reagent was cooled in an ice bath, and 73 g of N, N-dimethylformamide (1.0 mol) and 300 ml of tetrahydrofuranFuran mixture to control the reaction temperature is not higher than 30 degrees, dropping is completed at room temperature for 5 hours. After completion of the reaction1000 ml of saturated ammonium chloride solution for 1 hour hydrolysis, and then separated from the organic phase, the aqueous phase extracted with ethyl acetate aThe organic phase was washed with 500 mL of saturated brine and allowed to stand for separation. The organic phase was stirred and dried with 50 g of anhydrous sodium sulfate1 hour, filtered and the filtrate was concentrated to dryness under reduced pressure to give 2, 3-dimethylbenzaldehyde in a yield of 93percent and a purity of 95percentUnder the protection of nitrogen, added in a reaction bottle 24 g mgnesium filings (1mol) and 160 ml of tetrahydrofuran, under stirring at room temperature is dropped to 18.5 g 2, 3-dimethyl-chlorobenzene (0.1mol) and 100 ml of a mixed solution of tetrahydrofuran, initiate the reaction, and then to continue dropping 166.5 g 2, 3-dimethyl-chlorobenzene (0.9mol) and 1000 ml of a mixed solution of tetrahydrofuran, completion of the dropping, reflux reaction 5 hours. With ice-bath cooling the resulting Grignard reagent, dropping 73 g N, N-dimethyl formamide (1.0mol) and 300 ml of a mixed solution of tetrahydrofuran, controlling the reaction temperature is not higher than 30 degrees, the dropping to the reaction at room temperature 5 hours. Reaction of adding the end of 1000 ml of saturated ammonium chloride solution to hydrolyze 1 hour, the organic phase is separated, the aqueous phase is extracted with ethyl acetate once, combined with the phase, using 500 ml saturated salt water washing, layering, organic phase with 50g mixing and drying by anhydrous sodium sulfate 1 hour, filtered, filtrate concentrated to dry, is 2, 3-dimethoxy benzaldehyde, the yield is 82percent, the purity of 85percent.

The major component of the umbel rays oil.

Molecular Weight:134.17
XLogP3:2.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:134.073164938
Monoisotopic Mass:134.073164938
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes