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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
69877-38-9

(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal synthesis

14synthesis methods
(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dien-1-ol

63650-98-6

(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal

69877-38-9

GENERAL METHOD: Sodium carbonate (4.77 g, 45 mmol) and activated manganese dioxide powder (3.91 g, 45 mmol) were added to a vigorously stirred solution of alcohols 27-31 (2.2 mmol) in dichloromethane (45 mL). The resulting suspension was stirred at room temperature until the reaction was complete (monitored by thin layer chromatography) and subsequently filtered through a diatomaceous earth pad. The filtrate was evaporated to dryness to obtain the residue. The residue was purified by fast column chromatography to afford allyl aldehydes 32-36 (only the 2E,4E-isomer was plotted).

(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dien-1-ol

63650-98-6
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(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal

69877-38-9
43 suppliers
$156.00/100mg

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Yield:69877-38-9 90%

Reaction Conditions:

with manganese(IV) oxide;sodium carbonate in dichloromethane at 25; for 1 h;

Steps:

4.1.5. General procedure for the MnO2-mediated oxidations of allylic alcohols

General procedure: To a vigorously stirred solution of alcohols 27-31 (2.2 mmol) in CH2Cl2 (45 mL), Na2CO3 (4.77 g, 45 mmol) and activated MnO2 powder (3.91 g, 45 mmol) were added. The resulting suspension was stirred at ambient temperature to complete the reaction (monitored by TLC) and then passed through a celite pad. The filtrate was evaporated to dryness to leave a residue. Allylic aldehydes 32-36 (only the 2E,4E-isomer is drawn) were obtained from this residue through FCC purification.

References:

Magoulas, George E.;Bariamis, Stavros E.;Athanassopoulos, Constantinos M.;Haskopoulos, Anastasios;Dedes, Petros G.;Krokidis, Marios G.;Karamanos, Nikos K.;Kletsas, Dimitris;Papaioannou, Dionissios;Maroulis, George [European Journal of Medicinal Chemistry,2011,vol. 46,# 2,p. 721 - 737] Location in patent:experimental part

4-Pentenal, 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylene-, (4E)-

478496-90-1
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2,4-Pentadienal, 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-, (2Z,4E)-

69877-39-0
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(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal

69877-38-9
43 suppliers
$156.00/100mg

References
5469-19-2 Synthesis
5-BROMO-1,2,4-TRIMETHYLBENZENE

5469-19-2
85 suppliers
$26.39/25g

(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal

69877-38-9
43 suppliers
$156.00/100mg

References
Benzene, 2-bromo-1,4,5-trimethyl-3-nitro-

154152-57-5
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(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal

69877-38-9
43 suppliers
$156.00/100mg

References
20469-61-8 Synthesis
2,3,5-TRIMETHYLANISOLE

20469-61-8
118 suppliers
$19.00/5g

(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal

69877-38-9
43 suppliers
$156.00/100mg

References