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Chemical Structure| 888325-29-9 Chemical Structure| 888325-29-9

Structure of 888325-29-9

Chemical Structure| 888325-29-9

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Product Details of [ 888325-29-9 ]

CAS No. :888325-29-9
Formula : C8H14O2
M.W : 142.20
SMILES Code : O=C1CC(C)(C)C(O)CC1
English Name :4-Hydroxy-3,3-dimethylcyclohexanone
MDL No. :MFCD18157601

Safety of [ 888325-29-9 ]

Application In Synthesis of [ 888325-29-9 ]

* 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 [ 888325-29-9 ]

[ 888325-29-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 131206-74-1 ]
  • [ 888325-29-9 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride In methanol; water at 20℃; 1.C C. 4-Hydroxy-3,3-dimethylcyclohexanone C. 4-Hydroxy-3,3-dimethylcyclohexanone A solution of 7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-ol (1.0 equiv.) in 2.0 N hydrochloric acid aqueous solution (3.7 equiv.) and MeOH (0.9 M) was stirred at room temperature overnight. TLC (petroleum ether: ethyl acetate=3:1) showed that the reaction was completed. The solvent was removed under reduced pressure, the resulting residue was basified with saturated aqueous sodium bicarbonate solution and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to give 4-hydroxy-3,3-dimethylcyclohexanone (88% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.69-3.71 (m, 1H), 2.42-2.45 (m, 2H), 2.09-2.25 (m, 1H), 2.04-2.08 (m, 4H), 1.91-1.95 (m, 1H), 0.98 (s, 6H)
85% With hydrogenchloride In acetone for 1h; Heating;
80% With hydrogenchloride; water In methanol at 20℃; for 1h; Intermediate 102: 4-Hydroxy-3,3-dimethylcyclohexanone To a solution of 7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-ol (For a preparation, see Intermediate 101 , 2.87 g, 15.41 mmol) in methanol (13 mL) was added HCl (2M aqueous solution, 30 mL, 60.0 mmol) and the reaction mixture stirred at rt overnight. The solvent was removed in vacuo and the residue neutralised (to ~ pH 7) with sat. aqueous NaHCO3 solution. The aqueous layer was extracted with ethyl acetate (2x 40 mL) and the combined organic layers were dried (hydrophobic frit) and concentrated in vacuo to give 4-hydroxy-3,3-dimethylcyclohexan-1-one (2.18 g, 12.26 mmol, 80 % yield) as a pale yellow oil. (0597) LCMS (2 min Formic): Rt = 0.54 min, [MH]+ = 143.0. (0598) 1H NMR (400 MHz, CDCl3) δ ppm 3.74 (dt, J=6.67, 3.46 Hz, 1 H) 2.37 - 2.67 (m, 2 H) 2.22 - 2.36 (m, 1 H) 2.04 - 2.18 (m, 2 H) 1.97 (dt, J=13.60, 6.80 Hz, 1 H) 1.02 (br. s, 6 H). Exchangeable proton not observed.
  • 3
  • [ 888325-29-9 ]
  • [ 888325-30-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 83 percent / N,N-diisopropylethylamine / CH2Cl2 / 72 h / 20 °C 2.1: potassium hydride / Heating 2.2: 93 percent / 3 h / Heating
  • 4
  • [ 888325-29-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 83 percent / N,N-diisopropylethylamine / CH2Cl2 / 72 h / 20 °C 2.1: potassium hydride / Heating 2.2: 93 percent / 3 h / Heating 3.1: 1,1,3,3-tetramethylguanidine / dimethylformamide / 25 h / 20 °C 3.2: 4-(dimethylamino)pyridine; triethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 20 °C 3.3: 25 percent / 2,4,6-collidine / xylene / 24 h / Heating
  • 5
  • [ 888325-29-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 83 percent / N,N-diisopropylethylamine / CH2Cl2 / 72 h / 20 °C 2.1: potassium hydride / Heating 2.2: 93 percent / 3 h / Heating 3.1: 1,1,3,3-tetramethylguanidine / dimethylformamide / 25 h / 20 °C 3.2: 4-(dimethylamino)pyridine; triethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 20 °C 3.3: 25 percent / 2,4,6-collidine / xylene / 24 h / Heating 4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / 20 °C 4.2: tetrahydrofuran; toluene / 5 h / Heating
  • 6
  • [ 888325-29-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 83 percent / N,N-diisopropylethylamine / CH2Cl2 / 72 h / 20 °C 2.1: potassium hydride / Heating 2.2: 93 percent / 3 h / Heating 3.1: 1,1,3,3-tetramethylguanidine / dimethylformamide / 25 h / 20 °C 3.2: 4-(dimethylamino)pyridine; triethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 20 °C 3.3: 25 percent / 2,4,6-collidine / xylene / 24 h / Heating 4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / 20 °C 4.2: tetrahydrofuran; toluene / 5 h / Heating
  • 7
  • [ 134409-06-6 ]
  • [ 888325-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / sodium borohydride / ethanol / 4 h / 20 °C 2: 85 percent / aq. hydrochloric acid / acetone / 1 h / Heating
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 1 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride / water; methanol / 20 °C
Multi-step reaction with 2 steps 1: methanol; sodium tetrahydroborate / 1 h / 0 - 20 °C 2: hydrogenchloride; water / methanol / 1 h / 20 °C
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.5h; Inert atmosphere; Large scale;

  • 8
  • [ 888325-29-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: (+/-)-4-hydroxy-3,3-dimethylcyclohexanone; benzylamine With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 5℃; for 3h; Stage #2: With sodium hydrogencarbonate In dichloromethane at 0 - 5℃; 16.2 (0.43 g, 3.0 mmol) 4-Hydroxy-3,3-dimethylcyclohexanone (example 16, step 1) was dissolved in dichloromethane (15 ml) and the mixture was cooled to 0-5° C. Sodium triacetoxyborohydride (640 mg, 3.0 mmol, 1.0 equiv.), benzylamine (400 μl, 3.63 mmol, 1.2 equiv.) and acetic acid (173 μl, 3.0 mmol, 1.0 equiv.) were added at 0° C. The mixture was stirred for 3 hours at 0-5° C.The reaction mixture was treated with sat. NaHCO3 solution and extracted twice with a small volume of CH2Cl2. The organic layers were loaded directly to silica gel column and the crude material was purified by flash chromatography on silica gel (20 gr, methanol/dichloromethane gradient, 0:100 to 10:90). The desired diast. rac 4-benzylamino-2,2-dimethyl-cyclohexanol (420 mg, 60% yield) was obtained as a colorless semi solid, MS: m/e=234.2 (M+H+).
 

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