Phenylpropyl ether

Superior yields of ethers from aldehydes are obtained by the use of several other electrophilic species. The addition of 5 mol% of trityl perchlorate to a mixture of triethylsilane and 3-phenylpropanal in dichloromethane at 0° produces an 83% yield of bis-(3-phenylpropyl) ether within 10 minutes (Eq. 176),329 Reductive polycondensation of isophthalaldehyde occurs with two equivalents of triethylsilane in the presence of 10 mol% of trityl perchlorate to give 40-72% yields of polyether with average molecular weights ranging from 6,500 to 11,400 daltons (Eq. 177).337 Addition of one equivalent of an alkoxytrimethylsilane to the reaction mixture produces unsymmetrical ethers in good to excellent yields. Thus, a mixture of (ii)-cinnamaldehyde, 3-phenylpropoxytrimethylsilane, and triethylsilane in dichloromethane reacts under the influence of a catalytic amount of trityl perchlorate to give the unsymmetrical ether in 88% yield (Eq. 178).329... 

Heptyl 3-Phenylpropyl Ether [Electrogenerated Acid-Promoted Reduction of an Aldehyde to an Unsymmetrical Ether].333 A mixture of 1-heptanal (1.0 mmol), 3-phenylpropoxytrimethylsilane (1.2 mmol), tetra-n-butylammonium perchlorate (0.1 mmol), and lithium perchlorate (0.1 mmol) was dissolved in CH2CI2 (3 mL) in an undivided cell. The mixture was electrolyzed under constant current (1.67 mA cm-2) with platinum electrodes at ambient temperature. After 5 minutes, dimethylphenylsilane (1.2 mmol) was added drop-wise and the electrolysis was continued (0.06 Faraday/mol). After completion of the reaction, one drop of Et3N was added and the solution was concentrated. The residue was chromatographed on Si02 to give 1-heptyl 3-phenylpropyl... 

Benzaldehydes, alkane reduction, 70-72 Benzoic acids, reduction of, 50 Benzyl-3-phenylpropyl ether [trityl... 

C6H5CH2CH2CH2OH 2.CH3CH,Br QH5CH2CH2CH2OCH2CH3 3-Phenyl-l-propanol Ethyl 3-phenylpropyl ether... 

Percec V, Peterca M, Sienkowska MJ, Hies MA, Aqad E, Smidrkal J, Heiney PA (2006) Synthesis and retrostructural analysis of libraries of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers. J Am Chem Soc 128(10) 3324—3334. doi 10.1021/ja060062a... 

Percec V, Peterca M, Rudick JG, Aqad E, Imam MR, Heiney PA (2007) Self-assembling phenylpropyl ether dendronized helical polyphenylacetylenes. Chem Eur J 13 (34) 9572-9581. doi 10.1002/chem.200701008... 

Grape Allyl salicylate Cinnamyl anthranilate Guaiol acetate Isobutyl anthranilate Isovalerophenonc Octyl isobutyrate Phenylpropyl acetate, ether. 

A stirred solution of 0.0158 mole of ethyl-a-[(l-carboxyethyl)amino] benzenebutanoate hydrochloride in 200 ml of methylene chloride was treated successively with 1.60 g (0.0158 mole) of triethylamine, 0.0158 mole of 1-hydroxybenzotriazole, 0.0158 mole of l,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid and then with 0.0158 mole of dicyclohexylcarbodiimide in 10 ml of methylene dichloride. Dicyclohexylurea gradually separated. The mixture was allowed to stand at room temperature overnight. Hexane (300 ml) was added and the urea was filtered. The filtrate was washed with 250 ml of saturated sodium bicarbonate, dried over sodium sulfate and concentrated to remove solvent. The viscous residue was triturated with 50 ml of ether and filtered to remove insolubles. The filtrate was concentrated to give 2-[2-[[l-(ethoxycarbonyl)-3-phenylpropyl]amino]-l-oxopropyl]-l,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid. 

Methochloride, CggHyCINO, I-(3-eyctohexyt-3-hydroxy-3-phenylpropyl)-l-methylpyrrolidinlum chloride, tricyclamol chloride, Etorine chloride, Lergine chloride, Tricotoid chto. ride. Crystals front nitroethane, mp 159-164°. Moderately sol in water, alcohol. Practically insol in ether. 

---