Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester synthesis
- Product Name:Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester
- CAS Number:153559-48-9
- Molecular formula:C25H30O2
- Molecular Weight:362.5
1779-49-3
![Methyl 4-[(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl]benzoate](/CAS/GIF/153559-45-6.gif)
153559-45-6
153559-48-9
Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-carbonyl)benzoate was synthesized by Wittig reaction using methyltriphenylphosphonium bromide and methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate as starting materials. During the synthesis, crystals of compound 35 were found to be suitable for X-ray diffraction analysis. To complete the synthesis of bexarotene, compound 35 was first subjected to Friedel-Crafts acylation using crude monomethyl terephthaloyl chloride (36) to give ketone 37. Subsequently, ketone 37 was converted to olefinic ester 38 by Wittig reaction. finally, olefinic ester 38 was subjected to saponification in the presence of potassium hydroxide followed by acidification with aqueous hydrochloric acid. to obtain the target product bexarotene (39) (Scheme 2).
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