40275-47-6

Upstream product

• 97-53-0 4-allylguaiacol 
• 201230-82-2 carbon monoxide 
• 111-92-2 dibutylamine 
• 97-54-1 2-methoxy-4-propenylphenol 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 64-17-5 ethanol 

Relevant academic research and scientific papers

One-pot hydroformylation/O-acylation of propenylbenzenes for the synthesis of polyfunctionalized fragrances

A process involving the hydroformylation/O-acylation of propenylbenzenes with a phenolic group is described for eugenol, isoeugenol, chavicol, propenyl guaethol, 2-allylphenol, and 2-allyl-6-methylphenol. The reactions occur in parallel, under the same reaction conditions in anisole, a solvent with an impressive sustainability rank comparable to those of ethanol and water. The products contain formyl and acetoxy moieties, both established olfactory groups in flavor and fragrance industry, and present potential as new fragrance components with less allergenic properties. To the best of our knowledge, this is the first time that a one-pot process involving hydroformylation combined with further functionalization in a remote site is described.

An electrostatically-anchored rhodium(I) catalyst for the hydroformylation and tandem hydroformylation/acetalization of biorenewable allyl benzenes

A rhodium catalyst anchored in a commercial anion exchange resin (IRA900/TPPMS/Rh) was prepared straightforwardly through a simple protocol from readily available precursors. The material was used as a heterogeneous catalyst for the hydroformylation and tandem sequence hydroformylation/acetalization of eugenol and estragole under mild conditions. The regioselectivity for linear products was ca. 62percent, but for the allyl benzenes the branched isomer are also valuable. The performance of the anchored catalyst in hydroformylation was comparable to that of the conventional homogeneous rhodium system; however, its efficiency in the acetalization step was significantly higher. The material can be separated from the reaction solutions by decantation and re-used without a significant loss in activity and selectivity. This simple catalytic method represents an economically attractive route to commercially valuable fragrance compounds starting from the substrates easily available from natural bio-renewable sources.

Rhodium catalyzed aqueous biphasic hydroformylation of naturally occurring allylbenzenes in the presence of water-soluble phosphorus ligands

The rhodium-catalyzed hydroformylation of eugenol was performed in aqueous biphasic systems using various water soluble phosphines: TPPTS (triphenylphosphinetrisulphonated); BDPPETS (bisdiphenylphosphinoethanetetrasulphonated), BDPPPTS (bisdiphenylphosphi

Rhodium catalyzed aqueous biphasic hydroformylation of naturally occurring allylbenzenes in the presence of water-soluble phosphorus ligands

The rhodium-catalyzed hydroformylation of eugenol was performed in aqueous biphasic systems using various water soluble phosphines: TPPTS (triphenylphosphinetrisulphonated); BDPPETS (bisdiphenylphosphinoethanetetrasulphonated), BDPPPTS (bisdiphenylphosphi

Hydroaminomethylation of eugenol with di-n-butylamine catalyzed by rhodium complexes: Bringing light on the promoting effect of Br?nsted acids

The hydroaminomethylation of eugenol with di-n-butylamine was performed employing a bis[(1,5-ciclooctadiene)(μ-methoxy)rhodium(I)] as pre-catalyst. In the absence of phosphines, the catalyst was efficient in the process, but the regioselectivity for amines was poor. For phosphine-promoted catalyst, the chemoselectivity at the hydroformylation step improved, but the hydrogenation of enamine intermediates was hampered. The regioselectivity within the class of amines was surprisingly high (>96%) for the linear product. The addition of triflic acid (10-20 mol%) improved significantly the efficiency of HAM. Employing the 2,2′-bis((diphenylphosphino)methyl)-1,1′-binaphthyl as ancillary and triflic acid as a promoter, the linear product was obtained in up to 93% yield.

Biphasic hydroformylation of substituted allylbenzenes with water-soluble rhodium or ruthenium complexes

The water-soluble complexes [Rh(CO)(Pz)(L)]2 and [HRu(CO)(CH3CN)(L)3][BF4] [L = TPPMS (m-sulfonatophenyl-diphenylphosphine) and TPPTS (tris-m-sulfonato- phenylphosphine)] were used for the first time as catalyst precursors for the hydroformylation of eugenol, estragole, safrole and trans-anethole under moderate conditions in biphasic media. Under mild reaction conditions the substrates showed the following reactivity order: eugenol > estragole ≈ safrole > trans-anethole. The use of cetyl-trimethylammonium chloride (CTAC) as phase transfer agent inhibits the isomerization reaction, reaching high selectivity for the hydroformylation products (80-94%). The catalytic phase can be recycled up to four times with a decrease in the activity over time but maintaining its high selectivity.

Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes

The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)2acac/ultranox626/CO/H2/CH2Cl2 led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H3PO4 enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process.