Cinnamyl esters

The cinnamyl ester can be prepared from an activated carboxylic acid derivative and cinnamyl alcohol it is cleaved under nearly neutral conditions [Hg(OAc)2, MeOH, 23°, 2-4 h KSCN, H2O, 23°, 12-16 h, 90% yield]. 

The cinnamyl ester can be prepared from an activated carboxylic acid derivative and cinnamyl alcohol or by transesterification with cinnamyl alcohol in the presence of the H-Beta Zeolite (toluene, reflux, 8 h, 59-96% yield). It is cleaved under nearly neutral conditions [Hg(OAc)2, MeOH, 23°, 2-A h KSCN, H2O, 23°, 12-16 h, 90% yield]or by treatment with Sulfated-Sn02, toluene, anisole, reflux. The latter conditions also cleave crotyl and prenyl esters. 

Pd(OAc)2, TPPTS, CH3CN, H2O, Et2NH, 30 min, 89-99% yield. Deprotection can be achieved in the presence of a prenyl or cinnamyl ester, but as the reaction times increase, these esters are also cleaved.Prenyl carbamates and allyl carbonates are cleaved similarly. 

Toluenesulfonyl)ethyl Ester 23. /-Butyl Ester 27. Cinnamyl Ester... 

It may be prepared synthetically by reducing cinnamic aldehyde diacetate, and saponifying the resulting cinnamyl esters. Cinnamic alcohol is a crystalline body, although commercial specimens frequently contain traces of impurities which prevent crystallisation. It has the following characters —... 

Cinnamic alcohol can be dehydrogenated to give cinnamaldehyde and oxidized to give cinnamic acid. Hydrogenation yields 3-phenylpropanol and/or 3-cyclo-hexylpropanol. Reaction with carboxylic acids or carboxylic acid derivatives results in the formation of cinnamyl esters, some of which are used as fragrance materials. 

Uses. Cinnamic alcohol is valuable in perfumery for its odor and fixative properties. It is a component of many flower compositions (lilac, hyacinth, and lily of the valley) and is a starting material for cinnamyl esters, several of which are valuable fragrance materials. In aromas, the alcohol is used for cinnamon notes and for rounding off fruit aromas. It is used as an intermediate in many syntheses (e.g., for pharmaceuticals such as the antibiotic Chloromycetin). 

Tolu balsam resinoid contains a fairly large amount of benzyl and cinnamyl esters of benzoic and cinnamic acid [284a, 800-800b]. 

Chem. Abstr. Name 3-Phenyl-2-propen-l-ol, 2-aminobenzoate lUPAC Systematic Name Anthranilic acid, cinnamyl ester Synonyms Cinnamyl alcohol anthranilate 3-phenyl-2-propenyl 2-aminobenzoate 3-phenyl-2-propenyl anthranilate... 

Demethoxyabresoline (67) was obtained as a noncrystalline solid. Spectroscopic investigation revealed the presence of a phenolic OH, a 1-phenyl-quinolizidine system, and a trans-cinnamyl group. The stereochemistry at C-l, C-3, and C-5 was the same as in abresoline. The molecular formula C25H29N05 was established by mass spectrometry. The presence of fragment ions at m/e 259 (M —164) and 258 was characteristic of p-hydroxy-cinnamyl esters of the phenylquinolizidol (63a). The assigned structure 68 was confirmed by basic hydrolysis to 63a and p-hydroxycinnamic acid as well as by catalytic hydrogenation to a known dihydro derivative (52). 

D 1.047-1.051, refr index 1.539-1.543, flash p 244°F. Misc with chloroform, ether, fixed oils insol in glycerin, water 264°. SYNS ACETIC ACID, CINNAMYL ESTER FEMA No, 2293 Y-PHENYLALLYL ACETATE 3-PHENYL-2-PROPEN-l-YL ACETATE... 

SYNS BUTYNOIC acid, 3-PHENYL-2-PROPENYL ESTER BUTYRIC ACID, CINNAMYL ESTER PHENYLPROPENYL n-BUTYRATE... 

FORMIC ACID, CINNAMYL ESTER 3-PHENYL-2-PROPEN-l-YL FORMATE... 

SYNS FEMA No. 2301 3-PHENYL-2-PROPENYL PROPIONATE 3-PHENYL-2-PROPENM-YL PROPIONATE PROPIONIC ACID, CINNAMYL ESTER... 

ACETIC ACID, CINNAMYL ESTER see CMQ730 ACETIC ACID, CITRONELLYL ESTER see AAUOOO ACETIC ACID, COBALT(2+) SALT see CNCOOO ACETIC ACID, COBALT(2+) S. LT, TETRAHYDIL TE see CNA500... 

ANTHRANIUC ACID, CINNAMYL ESTER see API750 ANTHRANIUC ACID, METHYL ESTER see APJ250 ANTHRANIUC ACID, PHENETHYL ESTER see APJ500... 

BUTYRHODANID (GERMAN) see BSN500 n-BUTYRIC ACID see BSWOOO BUTYRIC ACID ANHYDRIDE see BSW550 n-BUTYRIC ACID ANHYDRIDE see BSW550 BUTYRIC ACID, CINNAMYL ESTER see CMQ800 BUTYRIC ACID, a-a-DIMETHYLPHENETHYL ESTER see BEL850... 

FORMIC ACID, CINNAMYL ESTER see CMR500 FORi nC ACID, CITRONELLYL ESTER see CMT750 FORMIC ACID-3,7-DIMETHYL-6-OCTEN-1-YL ESTER see CMT750... 

M K2CO3, MeOH, CH2CI2, 86% yield. A cinnamyl ester was retained."... 

K-10 clay, toluene, 1,4-dimethoxybenzene or anisole, heat, 87-98% yield. Microwave heating was also effective. Cinnamyl esters were cleaved similarly. 

H-(3-zeolite, anisole, toluene, reflux, 1.5-8 h, 70-90% yield. Cinnamyl esters are also cleaved in excellent yield, but allyl esters give mixed results with aliphatic allyl esters showing no cleavage. ... 

Pd(0Ac)2, TPPTS, CH3CN, H2O, EtjNH, 96-100% yield. The allyl carbamate (alloc) group can be cleaved in the presence of the prenyl ester. These conditions will also cleave allyl carbonates, cinnamyl esters, and prenyl carbamates. ... 

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