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Chemical Structure| 32565-44-9 Chemical Structure| 32565-44-9

Structure of 32565-44-9

Chemical Structure| 32565-44-9

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Product Details of [ 32565-44-9 ]

CAS No. :32565-44-9
Formula : C12H18O2
M.W : 194.27
SMILES Code : OC1=C(C)C=C(C(C)(C)C)C=C1OC
MDL No. :MFCD00561997

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Application In Synthesis of [ 32565-44-9 ]

* 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 [ 32565-44-9 ]

[ 32565-44-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 507-20-0 ]
  • [ 2896-67-5 ]
  • [ 32565-44-9 ]
YieldReaction ConditionsOperation in experiment
96.6% aluminum (III) chloride; In 1,2-dichloro-ethane; Preparation of 4-tert-butyl-<strong>[2896-67-5]2-methyl-6-methoxyphenol</strong> from 2-methyl-6- methoxypehnol via a Friedel-Craft reaction[00108] A 250 ml of flask is charged with 2-methoxy-6-methylcatechol (5.0 g, 36.2 mmol), ethylene dichloride (30 mL). To the stirred solution is added anhydrous aluminum chloride (0.72 g, 5.4 mmol, 0.15 equiv.), followed by the drop- wise addition of a solution of 2-chloro-2-methylpropane (4.4 ml, 39.8 mmol, 1.1 equiv.) in ethylene dichloride (30 mL). The mixture is stirred overnight, and then quenched with IN HC1. After separation, the aqueous layer is extracted with ether. The combined organic solution is washed with brine, and dried over magnesium sulfate. After filtration, the filtrate is concentrated and dried in vacuo to yield 6.3 g (96.6 %) of the product as an off-white solid. NMR: 6.75 (s, 2H), 5.56 (s, 1H), 3.87 (s, 3H), 2.25 (s, 3H), 1.29 (s, 9H).
  • 2
  • [ 2896-67-5 ]
  • [ 75-65-0 ]
  • [ 32565-44-9 ]
  • C12H18O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; at 20℃; for 12h; To a stirring solution of 5-methyl-2-methoxyphenol (1 eq, 1380 mg, 10 mmol) in t-BuOH 30 mL at rt under was added H2SO4 5 mL, the reaction mixture was stirred for 12 hours at rt, then 25 mL of H2O was added, then the aqueous phase was then extracted with equal amount of CH2Cl2 three times again, dried with anhydrous MgSO4, and concentrated by rotavaporor to obtained acrude mixture of product in 3 : 1 ratio obtained in 92 % yield. Then the mixture of two butylated were send for general procedure A directly without purification. After silica gel chromatography (EtOAc : hexanes = 1 : 7) of the crude mixture from the D-A reaction, 1360 mg (56%) of compound S20 and 456 mg (19%) of compound S21 were obtained both as a yellowish oil.
 

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