Preparation method and application of 3,7,11-trimethyl-2,4,6,10-dodecanyl tetraenol acetate
A technology of dodecyltetraenol acetate and 10-, which is applied in the preparation of carboxylic acid esters, hydroxyl compounds, organic compounds, etc., can solve the problems of difficult industrialization, complicated process, and high cost, and achieve The effect of simple operation, simple process route and low cost
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Embodiment 1
[0026] Preparation of Geranyl Chlorotriphenylphosphonium Salt
[0027] Under nitrogen protection, 172 grams of geranyl chloride (1 mole), 280 grams of triphenylphosphine (1.07 moles) and 500 milliliters of chlorobenzene were sequentially added to a 1000-milliliter four-necked flask equipped with mechanical stirring and a reflux condenser. After cooling and filtering for 5 hours, the solid was washed with 100 ml of dichloromethane and dried to obtain 416.6 g of geranyl chloride triphenylphosphonium salt with a yield of 96.0%.
[0028] Product structure verification:
[0029] 1 HNMR (δ, ppm, 400MHz, MeOD): 1.382 (d, 3H, J=3.6, CH 3 );1.507,1.564(s,6H,2CH 3 );2.032-2.044(m,4H,2CH 2 );4.218-4.276(m,2H,CH 2 );4.918(q,1H,J=6.8,CH);5.134-5.183(m,1H,CH);7.722-7.824,7.875-7.880(m,15H,Ar-H)
[0030] 13CNMR(δ,ppm,100MHz,MeOD):15.68,15.71;16.55;22.35,22.85;24.64;25.44,25.47;39.18,39.21;108.30,108.40;118.12,118.97;123.45;130.04;130.16;130.27;131.64;133.64 ;133.73;134.94;134.97;146.4...
Embodiment 2
[0032] Preparation of 3,7,11-trimethyl-2,4,6,10-dodecanyl tetraenol acetate
[0033] Under nitrogen protection, 47.7 grams of geranyl chloride triphenylphosphonium salt (0.11 moles), 150 milliliters of methanol and 15.9 grams of sodium carbonate (0.15 moles) were added successively in a 250 milliliter four-necked bottle equipped with mechanical stirring and a thermometer, and then Add 14.2 g of pentacarbonaldehyde (0.1 mole) dropwise at 50°C, and the dropwise addition is completed in 10 minutes. TLC detection (developing agent: ethyl acetate: petroleum ether = 2:8) reacts completely in about 24 hours. Remove inorganic salts by filtration, evaporate methanol under reduced pressure, add cyclohexane and stir for 0.5 hours, remove triphenoxyphosphine by filtration, evaporate the solvent to dryness, collect fractions at 185-189°C / mmHg under reduced pressure to obtain 22.6 grams of light yellow transparent liquid, the gas phase content 95.3%, yield 82.2%.
[0034] Product structure...
Embodiment 3～10
[0040] Preparation of 3,7,11-trimethyl-2,4,6,10-dodecyltetraenol acetate by condensation under different bases and temperatures
[0041] Under nitrogen protection, a certain amount of geranyl chloride triphenylphosphonium salt, a certain amount of alkali and 150 ml of methanol were sequentially added to a 250 ml four-necked bottle equipped with mechanical stirring and a thermometer, and then 14.2 ml of methanol was added dropwise at a certain temperature. gram of pentacarbonaldehyde (0.1 mole), the dropwise addition was completed in 10 minutes, and the reaction was complete by TLC detection. Filter to remove inorganic salts, distill under reduced pressure to recover methanol, add cyclohexane and stir for 0.5 hours, filter to remove triphenoxyphosphine, evaporate to dryness, collect fractions at 185-189°C / mmHg under reduced pressure, analyze by gas phase, and calculate the yield, the results are as follows surface.
[0042]
[0043] The product nuclear magnetic spectrum tha...
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