A kind of method for preparing 4-tert-butylphenylethanol
A technology of tert-butyl benzene and tert-butyl methyl phenethyl carbonate is applied in the field of preparing 4-tert-butyl phenethyl alcohol, and can solve the problems of expensive bromine, flammable and explosive ethylene oxide and the like , to avoid high risks, low cost, and easy access to raw materials
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Embodiment 1
[0020] The synthesis of embodiment 1 methylphenethyl carbonate
[0021] The reaction formula is:
[0022]
[0023] Dissolve phenylethyl alcohol (12.2g, 0.1mol) in ethyl acetate (50ml), add triethylamine (12.1g, 0.12mol), cool with ice water to 0-5°C, maintain this temperature, add methyl chloroformate dropwise Ester (10.4g, 0.11mol), after adding dropwise, the temperature was naturally raised to 25°C, the reaction was stirred, and the TLC plate was spotted until the phenylethanol disappeared, 30ml of water was added, the liquids were separated, the aqueous phase was extracted with 50ml of ethyl acetate, and the organic phase was Combined, washed with 30 ml of saturated sodium carbonate solution, dried over anhydrous magnesium sulfate, and evaporated the solvent to obtain 16.6 g of methyl phenethyl carbonate, with a yield of 92%.
Embodiment 2
[0024] The synthesis of embodiment 2 4-tert-butyl carbonate methylphenethyl ester
[0025] The reaction formula is:
[0026]
[0027] 1) Synthesis of methylphenethyl 4-tert-butylcarbonate
[0028] Methylphenethyl carbonate (9g, 0.05mol) was dissolved in dichloromethane (40ml), and anhydrous aluminum trichloride (16.7g, 0.125mol) was added, stirred at room temperature for 10min, heated to reflux, and isobutylene was slowly introduced, thin Follow the layer plate until the raw material point of methyl phenethyl carbonate disappears, add water (60 ml), separate the liquid, evaporate the solvent, and separate by silica gel column chromatography to obtain 9.7g of the product 4-tert-butyl methyl phenethyl carbonate , yield 82%.
[0029] 2) Synthesis of methylphenethyl 4-tert-butylcarbonate
[0030] Dissolve methylphenethyl carbonate (9g, 0.05mol) in dichloromethane (40ml), add anhydrous aluminum trichloride (16.7g, 0.125mol) and stir at room temperature for 10min, heat to refl...
Embodiment 3
[0033] The synthesis of embodiment 3 4-tert-butylphenylethanol
[0034] The reaction formula is:
[0035]
[0036] Add 4-tert-butylcarbonate methylphenethyl ester (11.8g, 0.05mol) into 30% sodium hydroxide solution (35g, 0.26mol), heat to reflux, and trace to 4-tert-butyl The raw material point of methylphenethyl carbonate disappeared, cooled to room temperature, added water (30 ml), separated the layers, extracted the aqueous phase with cyclohexane (30 ml), combined the organic phases, distilled off the solvent under normal pressure, and reduced pressure ( 5mmHg) Distilled (110°C) to collect the product 4-tert-butylphenylethanol to obtain 6.8 g, yield 76%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.38 – 7.33 (d, 2H), 7.18 (d, J = 8.3 Hz, 2H), 3.86 (t, J = 6.5 Hz,2H), 2.85 (t, J = 6.6 Hz, 2H), 1.33 (s, 9H).
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