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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List Tapinarof
79338-84-4

Tapinarof synthesis

8synthesis methods
The synthesis of Tapinarof begins with the aldol condensation of cinnamaldehyde (14.1) and ketone 14.2 to produce α, β, γ, δ-unsaturated ketone 14.3. Cinnamaldehyde (14.1) was subjected to Michael addition of diethyl malonate to give ketone 14.4 in 62% yield. Hydrolysis of 14.4 gave the malonic acid derivative 14.5. Treatment of 14.5 with a base at elevated temperature induced decarboxylation of the malonic acid molecule. Subsequently, the methyl ester was formed under the mediation of acid, and then the cyclic diketone 14.6 was obtained through Claisen condensation reaction in 79% yield over three steps. Chlorination of 14.6 with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) gave the penultimate intermediate 14.7 as a mixture of diastereoisomers in 96% yield. Treatment of the cyclic chlorodiketone 14.7 with tetraethylammonium chloride gave Tapinarof 14 in 86% yield.
Tapinarof
3,5-Dimethoxy-4-isopropyl-trans-stilbene

141509-20-8
12 suppliers
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Tapinarof

79338-84-4
156 suppliers
$79.00/10MG

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Yield:79338-84-4 85%

Reaction Conditions:

with pyridine hydrochloride in toluene at 90 - 180; for 2.5 h;Inert atmosphere;Large scale;

Steps:

3 Example 3 Preparation of phenenmod

Add 36kg of pyridine hydrochloride into the 100L reactor, under the protection of nitrogen, heat up to 90, add 10kg of E-4-isopropyl-3,5-dimethoxy-stilbene, and heat up to 180 or above and stir to react. About 2.5h, cool to about 90°C, add 50L of toluene, stir and cool, and filter the precipitated pyridine hydrochloride. The filtrate was washed twice with 5L of 1mol/L dilute hydrochloric acid, added with 1kg of activated carbon, heated and stirred for 0.5h, filtered, and concentrated to obtain a crude product.Recrystallization of n-heptane yields 7.6 kg of solid, with a yield of 85%.

References:

CN112661611,2021,A Location in patent:Paragraph 0029

115781-08-3 Synthesis
1,3-Benzenediol, 2-(1-Methylethyl)-5-(2-phenylethenyl)-

115781-08-3
16 suppliers
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Tapinarof

79338-84-4
156 suppliers
$79.00/10MG

References
2040-04-2 Synthesis
2',6'-Dimethoxyacetophenone

2040-04-2
146 suppliers
$14.00/1g

Tapinarof

79338-84-4
156 suppliers
$79.00/10MG

References
2-(2,6-dimethoxyphenyl)propan-2-ol

16929-70-7
1 suppliers
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Tapinarof

79338-84-4
156 suppliers
$79.00/10MG

References
Benzene, 1,3-dimethoxy-2-(1-methylethenyl)-

25108-61-6
2 suppliers
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Tapinarof

79338-84-4
156 suppliers
$79.00/10MG

References

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