2,2-Dimethyl-1,3-cyclopentanedione

The published procedure was followed. (Agosta, W. C.; Smith, A. B. J. Org. Chem. 1970, 35, 3856) A mixture of 2-methyl-1, 3-cyclopentanedione (10.025 g, 89.4 mmol, Aldrich), methyl iodide (6.0 mL, 96.4 mmol, Aldrich), and KOH (5.097 g, 90.8 mmol) in H2O (25 mL)/dioxane (75 mL) was heated at reflux. After 5 h, a solution of KOH (2 g) and MeI (2.4 mL) in H2O (5 mL)/dioxane (15 mL) was added and after another 3 h at reflux the solution was allowed to stir at room temperature overnight. In the morning, the reaction was continued by addition of a solution of KOH (2 g) and MeI (2.4 mL) in H2O (5 mL)/dioxane (15 mL) and heating at reflux. After 4 h, the mixture was allowed to cool to room temperature and was extracted with ether (1'100 mL, 3'75 mL). The combined ether extracts were evaporated, the residue combined with HCl (50 mL 10percent), and the resulting mixture was placed in a 120 C. oil bath until boiling was observed (ca. 15 min.). The mixture was then allowed to cool to room temperature, was neutralized by addition of NaHCO3 solution (150 mL, saturated) and the resulting mixture then extracted with CH2Cl2 (4'75 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated to leave a brown oil (10.474 g, 83 mmol, 93percent) which was used directly in the next step.Synthesized according to Agosta and Smith, J. Org. Chem., 35: 3856 (1970). A mixture of 2-methyl-1, 3-cyclopentanedione (10.025 g, 89.4 mmol, Aldrich), methyl iodide (6.0 mL, 96.4 mmol, Aldrich), and KOH (5.097 g, 90.8 mmol) in water (25 mL)/dioxane (75 mL) was heated at reflux. After 5 hours, a solution of KOH (2 g) and Mel (2.4 mL) in water (5 mL)/dioxane (15 mL) was added and after another 3 hours at reflux, the solution was stirred at room temperature overnight. A solution of KOH (2 g) and Mel (2.4 mL) in water (5 mL)/dioxane (15 mL) was added to the overnight reaction and heating at reflux. After 4 hours, the mixture was cooled to room temperature and extracted with ether (1×100 mL, 3×75 mL). The combined ether extracts were evaporated, the residue combined with 10percent HCl (50 mL), and the resulting mixture placed in a 120° C. oil bath until it began boiling (ca. 15 minutes). The mixture was cooled to room temperature, neutralized by addition of saturated NaHCO2-Methyl-1, 3-cyclopentanodione (7) (1 eq, 351 mmol, 39.4 g) was added to a solution of NaOH (1 eq, 351 mmol, 14.1 g) in water (75 mL) at 0 °C. After stirring for 15 min, the solution was evaporated under reduced pressure to dryness. Sodium salt of 7 was obtained with quantitative yield. To a suspension of sodium salt of 7 (47.4 g) in DMF (300 mL), MeI (1.5 eq, 526.5 mmol, 33.0 mL) was added and resulting mixture was stirred vigoriously overnight. Then, the reaction mixture was poured into water (2 L) and extracted with CHClThe published procedure was followed. (Brooks, D. W.; Hormoz, M.; Grothaus, P. G. J. Org. Chem. 1987, 52, 3223) A 35 C. (internal temperature) solution of D-glucose (106.73 g, 592 mmol, Aldrich) in H2O (690 mL) in a 4 L Erlenmeyer was treated with baker's yeast (71.065 g, Fleischmann's). The mixture was allowed to ferment for 2 h, then Synthesized according to Brooks, et al., J. Org. Chem., 52: 3223 (1987). A 35° C. (internal temperature) solution of D-glucose (106.73 g, 592 mmol, Aldrich) in water (690 mL) in a 4 L Erlenmeyer was treated with baker's yeast (71.065 g, Fleischmann's). The mixture was fermented for 2 hours, and

Molecular Weight:126.15
XLogP3:0.6
Hydrogen Bond Acceptor Count:2
Exact Mass:126.068079557
Monoisotopic Mass:126.068079557
Topological Polar Surface Area:34.1
Heavy Atom Count:9
Complexity:150
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes