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ChemicalBook CAS DataBase List 2-Allylphenol
1745-81-9

2-Allylphenol synthesis

12synthesis methods
Commercial production of 2 allylphenol is essentially the manufacture of a simple substituted phenol rather than a multi step pesticide synthesis. Industrial routes typically begin with ortho cresol or phenol derivatives, which undergo Friedel–Crafts type alkylation or transition metal catalysed allylation to introduce the allyl side chain at the ortho position. Catalysts such as Lewis acids or palladium complexes are used to control regioselectivity and suppress rearrangement to propenylphenols. The crude product is then purified by fractional distillation to remove unreacted phenol
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Yield:1745-81-9 98%

Reaction Conditions:

with methanol;1,3-disulfonic acid imidazolium hydrogen sulfate at 20; for 0.0666667 h;Green chemistry;

Steps:

General procedure for the deprotection of trimethylsilyl ethers
General procedure: A mixture of the substrate (1 mmol), ionic liquid [Dsim]HSO4 (6.5 mg, ∼0.02 mmol) in methanol (2 mL) was stirred at room temperature. After completion of the reaction (monitored by TLC), solvent was evaporated, water (1 mL) was added to the mixture, and stirred vigorously. Decantation of the mixture gave almost pure product(s). The products were characterized by comparison of their IR and NMR data. The ionic liquid was dried at 65 ◦C under vacuum to remove moisture, and then reused.

References:

Shirini, Farhad;Khaligh, Nader Ghaffari;Akbari-Dadamahaleh, Somayeh [Journal of Molecular Catalysis A: Chemical,2012,vol. 365,p. 15 - 23]

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