1-Methylcyclopropanecarboxylic acid

Colorless crystalline

To a 500 ml three-neck round bottom flask equipped with a mechanical stirrer, 6.9 g of sodium and 120 ml of anhydrous toluene were placed, The oil bath is heated to the metal sodium to melt, Stir quickly to form sodium sand.Under the conditions of nitrogen extraction of toluene, Then added100 ml of anhydrous tetrahydrofuran, To the reaction flask was added 16.9 g of 2, 2-dichloro-1-methylcyclopropylcarboxylic acid (0.1 mol)Thirty milliliters of a mixture of ethanol / water (19/3)After completion of the dropwise addition, And stirred at room temperature for an additional hour. Acidification: 50 ml of concentrated hydrochloric acid was added dropwise to pH = 1 with stirring, and the mixture was stirred for another half hour. Extracted with methylene chloride, and driedThe solvent was removed by evaporation and 9.26 g of 1-methylcyclopropylcarboxylic acid was obtained in a yield of 92.6percent and a purity of & gt; 95percent.General procedure: To a 500 ml three-neck round bottom flask equipped with a mechanical stirrer, 6.9 g of sodium and 120 ml of anhydrous toluene were placed, The oil bath is heated to the metal sodium to melt, Stir quickly to form sodium sand.Under the conditions of nitrogen extraction of toluene, Then added100 ml of anhydrous tetrahydrofuran, To the reaction flask was added 16.9 g of 2, 2-dichloro-1-methylcyclopropylcarboxylic acid (0.1 mol)Thirty milliliters of a mixture of ethanol / water (19/3)After completion of the dropwise addition, And stirred at room temperature for an additional hour. Acidification: 50 ml of concentrated hydrochloric acid was added dropwise to pH = 1 with stirring, and the mixture was stirred for another half hour. Extracted with methylene chloride, and driedThe solvent was removed by evaporation and 9.26 g of 1-methylcyclopropylcarboxylic acid was obtained in a yield of 92.6percent and a purity of & gt; 95percent. The same procedure was followed using 2, 2-dibromo-1-methylcyclopropylcarboxylic acid in place of 2, 2-dichloro-1-methylcyclopropylcarboxylic acid to give 1-methylcyclopropylcarboxylic acid in a yield of 92.7percent and a purity of & gt; 95percent.To a 500 ml three-neck round bottom flask equipped with a mechanical stirrer, 6.9 g of sodium and 120 ml of anhydrous toluene were placed, The oil bath is heated to the metal sodium to melt, Stir quickly to form sodium sand.Under the conditions of nitrogen extraction of toluene, Then added100 ml of anhydrous tetrahydrofuran, Add to the reaction flask18.3gDichloro-1-methylcyclopropylcarboxylate(0.1 mol)Thirty milliliters of a mixture of ethanol / water (19/3)After completion of the dropwise addition, And stirred at room temperature for an additional hour. Acidification: 50 ml of concentrated hydrochloric acid was added dropwise to pH = 1 with stirring, and the mixture was stirred for another half hour. Extracted with methylene chloride, and driedDried, evaporated to remove the solvent, To give 1-methylcyclopropylcarboxylic acid 9.31 g, The yield was 93.1percentPurity & gt; 95percent.General procedure: To a 500 ml three-neck round bottom flask equipped with a mechanical stirrer, 6.9 g of sodium and 120 ml of anhydrous toluene were placed, The oil bath is heated to the metal sodium to melt, Stir quickly to form sodium sand.Under the conditions of nitrogen extraction of toluene, Then added100 ml of anhydrous tetrahydrofuran, Add to the reaction flask18.3gDichloro-1-methylcyclopropylcarboxylate(0.1 mol)Thirty milliliters of a mixture of ethanol / water (19/3)After completion of the dropwise addition, And stirred at room temperature for an additional hour. Acidification: 50 ml of concentrated hydrochloric acid was added dropwise to pH = 1 with stirring, and the mixture was stirred for another half hour. Extracted with methylene chloride, and driedDried, evaporated to remove the solvent, To give 1-methylcyclopropylcarboxylate 9.31 g, The yield was 93.1percentPurity & gt; 95percent. The same procedure was followed using methyl 2, 2-dibromo-1-methylcyclopropylcarboxylate in place of methyl 2, 2-dichloro-1-methylcyclopropylcarboxylic acid to give 1-methylcyclopropylcarboxylate in a yield of 92.7percent and a purity of & gt; 95percent.Add l-hydroxy-4-nitroisoquinoline (880.3 mmol; 167.4 grams) and POClTo a 500 ml three-neck round bottom flask equipped with a mechanical stirrer, 16.2 g of 1-methylcyclopropanecarbonitrile (0.2 mol) was added, 50 ml of 30percent sodium hydroxide solution.With stirring, After heating under reflux for 3 hours, cool down, 40 ml of concentrated hydrochloric acid was added dropwise to pH = 1 with stirring, Stir for another half hour.Extracted with methylene chloride, Dried, evaporated to remove the solvent, To give 17.4 g of 1-methylcyclopropylcarboxylic acid, The yield was 87percentPurity & gt; 95percent.To a 500 ml three-neck round bottom flask equipped with a mechanical stirrer, 19.8 g, 1-methylcyclopropylcarboxamide (0.2 mol), 50 ml of 30percent sodium hydroxide solution.With stirring, After heating under reflux for 3 hours, cool down, 40 ml of concentrated hydrochloric acid was added dropwise to pH = 1 with stirring, Stir for another half hour.Extracted with methylene chloride, dry, The solvent was removed by evaporation, To give 17.2 g of 1-methylcyclopropylcarboxylic acid, The yield was 86.percentPurity> 95percent (GC normalization method).

Molecular Weight:100.12
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:100.052429494
Monoisotopic Mass:100.052429494
Topological Polar Surface Area:37.3
Heavy Atom Count:7
Complexity:103
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes