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[ CAS No. 2408-37-9 ] {[proInfo.proName]}

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Chemical Structure| 2408-37-9
Chemical Structure| 2408-37-9
Structure of 2408-37-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2408-37-9 ]

CAS No. :2408-37-9 MDL No. :MFCD00045550
Formula : C9H16O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 140.22 Pubchem ID :-
Synonyms :

Safety of [ 2408-37-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235 UN#:1224
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2408-37-9 ]

* 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 [ 2408-37-9 ]

[ 2408-37-9 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 6153-05-5 ]
  • [ 2408-37-9 ]
  • [ 187409-93-4 ]
YieldReaction ConditionsOperation in experiment
80% With ethylmagnesium bromide In tetrahydrofuran at 0 - 20℃;
80% With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; 1 Step 1 1) First, a solution of 10 g of 2.2.6 trimethyl cyclohexanone in 5 ml of THF was stirred and mixed. 2) at 0-5 °C, preferably at 0 °C in 100 ml THF 11.2 ml (1.5 fold) (Z)-3-methylpent-2-en-4-yn-1-ol was stirred and then,in solution. Ethylmagnesiumbromide (3 folds) was added with a solution of 7 ml of etherial solution and stirred for 30 to 40 minutes until the temperature reached room temperature. 3) The mixture of 1) and 2) was saturated by exchanging ammonium chloride (NH4Cl) for 12 hours. (The reaction was stopped by adding a saturated aqueous solution of ammonia chloride). 4) This was purified on a silica gel column with hexane and ethylacetate solvent to obtain 13.5 g (yield 80%) of the product.
(i) EtMgBr, Et2O, CH2Cl2, (ii) /BRN= 1905593/; Multistep reaction;
With ethylmagnesium bromide 1.) THF, Et2O, RT, 30 min, 2.) THF, Et2O, overnight; Yield given. Multistep reaction;

  • 3
  • [ 583-60-8 ]
  • [ 74-88-4 ]
  • [ 2816-57-1 ]
  • [ 1193-47-1 ]
  • [ 2408-37-9 ]
YieldReaction ConditionsOperation in experiment
1: 5% 2: 1% 3: 89% With manganese(II) bromide; lithium hexamethyldisilazane In tetrahydrofuran for 14h; Ambient temperature;
1: 89% 2: 1% 3: 5% With manganese(II) bromide; lithium hexamethyldisilazane In tetrahydrofuran at 22℃; for 14h;
  • 8
  • [ 29684-56-8 ]
  • [ 2408-37-9 ]
  • [ 75-36-5 ]
  • 2-(2,6,6-trimethyl-cyclohex-1-enylethynyl)-benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydroxide; n-butyllithium; triethylamine; In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; hexane; dichloromethane; water; ethyl acetate; benzene; This colourless oil was dissolved in 5 ml of tetrahydrofuran. After the dropwise addition of 3.9 ml of butyl lithium (1.6 molar in hexane) at -78 C., the reaction mixture was stirred at this temperature for 30 minutes. A solution of 0.59 g of 2,2,6-trimethyl-cyclohexanone in 4 ml of tetrahydrofuran was dropped in and the reaction mixture was stirred at room temperature for 5 hours, resulting in a yellow solution. The yellow solution was poured onto ice water/10% aqueous ammonium chloride, extracted with hexane, dried over sodium sulfate and evaporated. The yellow, oily residue was purified by flash chromatography (SiO2, hexane/5 % ethyl acetate) to give 1.7 g of a yellow oil. The yellow oil was dissolved in 90 ml of tetrahydrofuran and stirred for 6 hours at room temperature with 28.8 ml of a 0.5 normal aqueous solution of potassium hydroxide. The reaction mixture was poured onto ice/water, extracted with ether, washed with water, dried and evaporated. Purification of the residue by flash chromatography (SiO2, hexane/ethyl acetate =7:3) and crystallization from ethyl acetate/hexane yielded 1.1 g of white crystals, m.p. 120-121 C. The white crystals were dissolved in 10 ml of tetrahydrofuran and sequentially treated with 679 mg of triethylamine and 400 mg of acetylchloride. After 4 hours of stirring at room temperature, the reaction mixture was poured onto ice/1N hydrogen chloride, extracted with ether, dried over sodium sulfate and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate -4:1) yielded 0.8 of a colourless oil. The colourless oil was dissolved in 13 ml of benzene and added to a solution of 1.3 g of Burgess-reagent (methoxycarbonylsulfamoyl-triethylammonium hydroxide, inner salt) in 40 ml of benzene. The reaction mixture was heated to 60 C. for 3 hours. After distilling off most of the solvent, the residue was dissolved in ice water and extracted with ether. The residue obtained after drying and evaporation of the solvent was purified by flash chromatography (SiO2, hexane/ethyl acetate =9:1) to give 0.7 g of a slightly yellow oil. This yellow oil was dissolved in 18 ml of ethanol and treated with a solution of 0.78 g of potassium hydroxide in 4 ml of water at 45 C. for 2.5 hours. The reaction mixture was poured onto ice/saturated ammonium chloride solution, extracted with ether, dried and evaporated. The residue was purified with medium pressure liquid chromatography (SiO2, hexane/ethyl acetate =9:1) to give 0.46 g of a slightly yellow oil. This yellow oil was dissolved in 20 ml of methylene chloride and treated with 1.6 g qf manganese dioxide for 15 hours under vigorous stirring at room temperature. The manganese dioxide was filtered off, the filtrate evaporated and the residue purified with medium pressure chromatography (Si)2, hexane/2% ethyl acetate) to give 225 mg of 2-(2,6,6-trimethyl-cyclohex-1-enylethynyl)-benzaldehyde as yellow oil which solidified in the cold.
  • 9
  • [ 2408-37-9 ]
  • [ 2914-69-4 ]
  • [ 1064557-69-2 ]
  • 10
  • [ 2408-37-9 ]
  • [ 42969-65-3 ]
  • [ 1064557-65-8 ]
  • 11
  • [ 2408-37-9 ]
  • [ 2032-35-1 ]
  • [ 472-66-2 ]
YieldReaction ConditionsOperation in experiment
93.7% Stage #1: Bromoacetaldehyde diethyl acetal With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In tetrahydrofuran at 10 - 15℃; for 3h; 2 Example 2: Preparation of (2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde (I) Under nitrogen protection, add 100 g of tetrahydrofuran, 5.3 g (0.22 mole) of magnesium powder, 2.2 g of bromoacetaldehyde diethyl acetal (II2), and 0.02 g of iodine into a 500 ml four-necked flask equipped with a stirring, thermometer and reflux condenser. After stirring at 30-40°C for 15 minutes to initiate the reaction, add dropwise a mixed solution of 37.0 grams (0.2 moles) of bromoacetaldehyde diethyl acetal (II2) and 100 grams of tetrahydrofuran at 30-35°C, and drop it in 2 hours. Thereafter, the reaction was stirred at 35-40°C for 1 hour. Cool to 0-5°C, keep the temperature at 10-15°C, add 28.0 g (0.2 mol) 2,2,6-trimethylcyclohexanone () dropwise, the addition is completed in 1 hour, then 10-15°C The reaction was stirred for 2 hours. Recover tetrahydrofuran by distillation under reduced pressure, add 100 grams of water and 100 grams of dichloromethane to the residue obtained, and acidify with 50% sulfuric acid until the pH of the system is 2.0-2.5. Stir at 20-25°C for 2 hours, stand still and separate. The aqueous phase was extracted twice with dichloromethane, 50 grams each time, the organic phases were combined, and the organic phase was distilled to recover the dichloromethane, and then under reduced pressure distillation (80-95°C/2-3mmHg) to obtain 31.1 grams of colorless transparent liquid (2 ,6,6-Trimethyl-1-cyclohexenyl)acetaldehyde (I), the gas phase purity is 99.5%, and the yield is 93.7%.
  • 12
  • [ 7252-83-7 ]
  • [ 2408-37-9 ]
  • [ 472-66-2 ]
YieldReaction ConditionsOperation in experiment
92.8% Stage #1: 1-bromo-2,2-dimethoxyethane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In tetrahydrofuran at 10 - 15℃; for 3h; 1 Example 1: Preparation of (2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde (I) Under the protection of nitrogen, add 100 g of tetrahydrofuran, 5.3 g (0.22 mole) of magnesium powder, 1.8 g of bromoacetaldehyde dimethylacetal (II1), and 0.02 g of iodine into a 500 ml four-necked flask equipped with stirring, thermometer and reflux condenser. After stirring for 15 minutes at 30-40°C to initiate the reaction, add dropwise a mixed solution of 32.0 g (0.2 moles) of bromoacetaldehyde dimethyl acetal (II1) and 100 g of tetrahydrofuran between 30-35°C, and finish the drop in 2 hours. Thereafter, the reaction was stirred at 35-40°C for 1 hour. Cool to 0-5°C, keep the temperature at 10-15°C, add 28.0 g (0.2 mol) 2,2,6-trimethylcyclohexanone () dropwise, the addition is completed in 1 hour, then 10-15°C The reaction was stirred for 2 hours. Recover tetrahydrofuran by distillation under reduced pressure, add 100 grams of water and 100 grams of dichloromethane to the residue obtained, and acidify with 50% sulfuric acid until the pH of the system is 2.0-2.5. Stir at 20-25°C for 2 hours, stand still and separate. The aqueous phase was extracted twice with dichloromethane, 50 grams each time, the organic phases were combined, and the organic phase was distilled to recover the dichloromethane, and then distilled under reduced pressure (80-95/2-3mmHg) to obtain 30.8 grams of colorless transparent liquid (2 ,6,6-Trimethyl-1-cyclohexenyl)acetaldehyde (I), the gas phase purity is 99.6%, and the yield is 92.8%.
  • 13
  • [ 4360-63-8 ]
  • [ 2408-37-9 ]
  • [ 472-66-2 ]
YieldReaction ConditionsOperation in experiment
93.1% Stage #1: 2-bromomethyl-1,3-dioxolane With iodine; magnesium In 2-methyltetrahydrofuran at 30 - 40℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In 2-methyltetrahydrofuran at 10 - 15℃; for 3h; 3 Example 3: Preparation of (2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde (I) Under the protection of nitrogen, into a 500 ml four-necked flask equipped with stirring, thermometer and reflux condenser, add 100 g of 2-methyltetrahydrofuran, 5.3 g (0.22 mole) of magnesium powder, and 2.3 g of bromoacetaldehyde ethylene acetal (II3) ), 0.02 g of iodine, stirred at 30-40°C for 15 minutes to initiate the reaction, 31.0 g (0.2 moles in total) of bromoacetaldehyde ethylene acetal (II3) and 100 g of 2-methyl were added dropwise between 30-35°C The mixed solution of tetrahydrofuran was dripped in 2 hours, and then stirred and reacted at 40-45°C for 1 hour. Cool to 0-5°C, keep the temperature at 10-15°C, add 28.0 g (0.2 mol) 2,2,6-trimethylcyclohexanone () dropwise, the addition is completed in 1 hour, then 10-15°C The reaction was stirred for 2 hours. Recover 2-methyltetrahydrofuran by distillation under reduced pressure. Add 100 grams of water and 120 grams of ethyl acetate to the residue obtained, and acidify with 50% sulfuric acid until the pH of the system is 2.0-2.5. Stir at 20-25°C for 2 hours, and let stand still Separate the layers, extract the aqueous phase twice with ethyl acetate, 50 grams each time, combine the organic phases, distill the organic phase to recover the ethyl acetate, and distill under reduced pressure (80-95°C/2-3mmHg) to obtain 30.9 grams of colorless Transparent liquid (2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde (I), gas phase purity 99.3%, yield 93.1%.
  • 14
  • [ 97-97-2 ]
  • [ 2408-37-9 ]
  • [ 472-66-2 ]
YieldReaction ConditionsOperation in experiment
90.7% Stage #1: chloroacetaldehyde dimethyl acetal With iodine; magnesium In ethylene dibromide at 30 - 45℃; for 3.41667h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In ethylene dibromide at 10 - 15℃; for 3h; 4 Example 4: Preparation of (2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde (I) Under the protection of nitrogen, add 100 g of tetrahydrofuran, 5.3 g (0.22 mole) of magnesium powder, 1.9 g of chloroacetaldehyde dimethylacetal (II4), and 0.02 g of iodine into a 500 ml four-necked flask equipped with stirring, thermometer and reflux condenser. , 2.0 grams of 1,2-dibromoethane, stirred at 35-45°C for 25 minutes to initiate the reaction, and dropwise add 23.0 grams (0.2 moles in total) of chloroacetaldehyde dimethylacetal (II4) and 100 at 40-45°C. The mixed solution of gram of tetrahydrofuran was dripped in 2 hours, and then stirred at 45-50°C for 1 hour. Cool to 0-5°C, keep the temperature at 20-25°C, add 28.0 g (0.2 mol) 2,2,6-trimethylcyclohexanone () dropwise, the addition is completed in 1 hour, then 10-15°C The reaction was stirred for 2 hours. Recover tetrahydrofuran by distillation under reduced pressure, add 100 grams of water and 100 grams of dichloromethane to the residue obtained, and acidify with 50% sulfuric acid until the pH of the system is 2.0-2.5. Stir at 20-25°C for 2 hours, stand still and separate. The aqueous phase was extracted twice with dichloromethane, 50 grams each time, the organic phases were combined, and the organic phase was distilled to recover the dichloromethane, and then distilled under reduced pressure (80-95/2-3mmHg) to obtain 30.1 grams of colorless transparent liquid (2 ,6,6-Trimethyl-1-cyclohexenyl)acetaldehyde (I), the gas purity is 99.2%, and the yield is 90.7%.
  • 15
  • [ 161023-01-4 ]
  • [ 2408-37-9 ]
  • [ 79-77-6 ]
  • [ 432-25-7 ]
YieldReaction ConditionsOperation in experiment
62% With oxygen In ethyl acetate at 80℃; Procedures for the Se/Fe3O4-catalyzed oxidative degradation ofpolyene β-Carotene was used as the example of polyene in the experiments. In the procedure, 30 mg of Se/Fe3O4 was added into 100 mL of β-carotene solution (0.01mol/L, EtOAc). O2 was then introduced into the mixture at the speed of 0.88 mL/s at 80 oC. The samples at the related reaction times were photographed and analyzed by UV-vis.
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