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Chemical Structure| 765-69-5 Chemical Structure| 765-69-5
Chemical Structure| 765-69-5

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CAS No.: 765-69-5

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Product Details of [ 765-69-5 ]

CAS No. :765-69-5
Formula : C6H8O2
M.W : 112.13
SMILES Code : CC1C(CCC1=O)=O
MDL No. :MFCD00001406
InChI Key :HXZILEQYFQYQCE-UHFFFAOYSA-N
Pubchem ID :13005

Safety of [ 765-69-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis [ 765-69-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 765-69-5 ]

[ 765-69-5 ] Synthesis Path-Downstream   1~7

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YieldReaction ConditionsOperation in experiment
93% 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.
93% With potassium hydroxide; In 1,4-dioxane; water; at 20℃;Reflux; 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 NaHCO3 solution (150 mL) and the resulting mixture 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.
36% 2-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 CHCl3 (4x100 mL). The combined extracts were washed with water (5x150 mL) and brine (200 mL), dried over anh. MgSO4 and concentrated under reduced pressure to yield dark oil (35.7 g). The oil was dissolved in 12percent HCl (330 mL) and refluxed for 1 h. The reaction mixture was cooled to rt, neutralized (to pH = 7) with 20percent aq. NaOH. Then, sat. aq. solution of Na2CO3 (100 mL) was added and the product was extracted with CHCl3 (4x100 mL). The combined extracts were washed with brine (100 mL), dried over anh. MgSO4 and evaporated under reduced pressure to afford 8 (15.79 g, 36percent). Physical state: pale brown solid.; IR (neat, cm-1): 2980, 1719, 1459, 1286, 993.; 1H NMR (400 MHz, CDCl3), delta (ppm): 2.80 (s, 4H), 1.15 (s, 6H).
With potassium hydroxide; In 1,4-dioxane; water; for 11h;Reflux; A mixture of 2-methylcyclopentane-l,3-dione (49.98 g, 446 mmol), potassium hydroxide (25.5 g, 455 mmol) and iodomethane (30.1 mL, 481 mmol) in dioxane (390 mL) and water (130 mL) was heated to reflux for 5 h. A biphasic mixture of potassium hydroxide (10.4 g), iodomethane (12.5 mL), water (26 mL) and dioxane (78 mL) was added. The mixture was heated at reflux for 3 additional hours and then stirred at ambient temperature overnight. Another portion of a biphasic mixture of potassium hydroxide (10.4 g), iodomethane (12.5 mL), water (26 mL) and dioxane (78 mL) was added. The mixture was heated at reflux for 3 h, cooled to room temperature and extracted with ether (600 mL, then 2x400 mL). The combined extracts were concentrated using a rotavap while keeping the bath temperature at or below room temperature to prevent loss of volatile product. The residue was treated with 10percent hydrochloric acid (250 mL) and placed in a 120 °C oil bath until it started to boil (~15 min). The mixture was cooled with an ice-water bath, diluted with water (250 mL) and treated with careful addition of sodium carbonate until carbon dioxide release stopped. The pH of the solution was 8-9. The mixture was extracted with dichloromethane (4x200 mL). The combined extracts were dried (MgS04), filtered and concentrated while keeping water bath at or below room temperature. The residue was further dried under vacuum briefly to remove residual solvent to give 2,2- dimethylcyclopentane-l,3-dione as tan solid (38.1 g, 68percent yield). XH NMR (400 MHz, chloroform-if) delta ppm 2.81 (4 H, s), 1.16 (6 H, s); LC retention time: 0.990 (analytical HPLC Method F).

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YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydroxide; sodium hydrogencarbonate; methyl iodide; In 1,4-dioxane; water; 2,2-Dimethyl-cyclopentane-1,3-dione (2). 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.
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  • [ 399-25-7 ]
  • [ 107-02-8 ]
  • C17H18FNO5 [ No CAS ]
 

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