Octyl 4-methoxycinnamate synthesis
- Product Name:Octyl 4-methoxycinnamate
- CAS Number:5466-77-3
- Molecular formula:C18H26O3
- Molecular Weight:290.4
Yield:5466-77-3 95%
Reaction Conditions:
with C43H54NO5P;palladium diacetate;triethylamine in water at 40; for 12 h;Heck Reaction;
Steps:
2 4.6.4. 2-Ethylhexyl (E)-3-(4-methoxyphenyl)acrylate
General procedure: Pd(OAc)2 (5.4 mg, 2.4102 mmol) and 1 (50 mg,7.2102 mmol) were combined in MeOH (10 mL) and treated bysonication at 25 C for 30 min, resulting in a hazy, yellow solution.Into 20-mL glass vials, 5.0 mL of this solution was delivered and allvolatiles were removed under vacuum, leaving a dry, yellow residueto be used directly for catalysis. To the dry, yellow catalystresidue, aryl iodide (0.60 mmol), acrylate (1.2 mmol), 5.0 mL H2O,and NEt3 (250 mL, 1.8 mmol) were added to the vial in the specifiedorder. The reactionwas thoroughly mixed via sonication for 10 minand subsequently stirred for 12 h at 40 C. At the completion of thereaction, all volatiles were removed under vacuum, and theremaining aqueous solution was extracted with ethyl acrylate(35 mL). The ethyl acrylate extracts were combined, dried withMgSO4, and all volatiles were removed under vacuum. The resultingcrude was purified via column chromatography.
References:
Roberts, Gina M.;Zhang, Shiyong;Zhao, Yan;Woo, L. Keith [Tetrahedron,2015,vol. 71,# 43,p. 8263 - 8270]
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