Hydroxy phenyl-2-butanone

ChHhOj, Mr 194.23, hot-tasting crystals, mp. 40°C, bp. 187 -188 °C (1.9 kPa). Z. is the pungent (hot) flavor principle in the oleoresin of ginger. 4-(4-hydroxy-phenyl)-2-butanone rheosmin, raspberry ketone, frambinone), CioHuOj, Mr 164.20, needles, mp. 82 C, is a component of raspberry flavor. It acts as a kairo-mone on the melon fly Dacus cucurbitae and related species. It is used as a flavor substance. 

Dragoco Company, Germany. Method of producing l-(4-hydroxy-phenyl)-butanone-3. UK Patents no. 876,684 and 876,685, 1959-60. 

CIC The powerful odour is dominated by 2-isobutyl thiazole and 3-pentanethiol. The green notes are lipid degradation products like (E)-2-hexenal, hexanal and higher unsaturated aldehydes, the pineapple-pear like fruity notes are derived from methyl hexanoate, ethyl-2-hexenoate and hexyl acetate. The spicy cinnamon notes are represented by 3-phenyl propyl acetate, cinnamyl acetate, methyl cinnamate, ethyl cinna-mate and ciimamaldehyde. Gamma-decalactone and 2,5-dimethyl-4-hydroxy-furan-3(2H)-one and 3-hydroxy-2-butanone add the sweet, creamy body. Beta-famesene, citronellol, 2-phenylethanol, beta-ionone add the sweet, floral, quincelike part and methyl benzoate and ethyl benzoate impart a characteristic medicinal, exotic topnote. 

Compounds include alcohols, acids, esters, carbonyls, ketones, and other hydrocarbons. However, a particular ketone l-(4-hydroxy phenyl)-3-butanone has an odor very much like raspberry [7,30]. This particiilar ketone, i.e., raspberry ketone, is sold under trade names Frambinon (Dragoco) and Oxyphe-nylon (IFF). In Hawai, the acetate of raspberry ketone is used under the trade name of Cue-Lure CAS No. [3572-06-3] to attract the harmhil melon-fly, Dacus Curcurbitae. 

This hydrochloride, on being dissolved in water and hydrogenated with hydrogen and a nickel catalyst, gave a good yield of hydrochloride of hydroxy-4 -phenyl-1-amino-2-ethanol melting, after crystallization from a mixture of ethyl alcohol and butanone-2, at from 177° to 179°C with decomposition. 

CN l-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]-l-piperidinyl]-l-butanone... 

HYDR0XY-3-NETHYL-1-PHENYL-1-BUTAN0NE BY CROSSED ALDOL REACTION (1-Butanone, 3-hydroxy-3-methyl -1-phenyl -)... 

Hydroxy-3-methyl-1-phenyl-1-butanone is too unstable to be purified by distillation, and is decomposed to acetophenone and acetone. 

A. Isopvopylidensaaetophenone. A 1-L, three-necked flask is fitted with a 100-mL pressure-equalizing dropping funnel, a mechanical stirrer and a condenser which is equipped with a two-way stopcock leading to a balloon of argon gas. To the flask is added a solution of 18,4 g of 3-hydroxy-3-methyl-1-phenyl-1-butanone (Note 1) in 60 mL of dry methylene chloride. The flask is cooled 1n an ice bath and 28.5 g of trlethylamine, a catalytic amount of 4-(N,N-dimethylamino)pyridine and 20 mL of methylene chloride are added. A solution of 25.8 g of trlfluoroacetic anhydride (Note 2) in 40 mL of methylene chloride Is added dropwlse over a period of 15 min, and the mixture is stirred for 2. 5 hr. ... 

HYDROXY-3-METHYL-1-PHENYL-1-BUTANONE BY CROSSED ALDOL REACTION... 

HYDROXY-3-METHYL-1-PHENYL-1-BUTANONE 1-BUTANONE, 3-HYDROXY-3-METHYL-1-PHENYL- (43108-74-3), 65, 6, 12 1-(3-HYDROXY-2-METHYL-3-PHENYLPROPANOYL)PIPERIDlNE, ERYTHRO PIPERIDINE, 1 -(3-HYDROXY-2-METHYL-1-OXO-3-PHENYLPROPYL)-, R, R )-( )- (99114-36-0), 69, 44 N-Hydroxymethylphthalimide Phthalimide, N-(hydroxymethyl)- ... 

As mentioned previously, the cyclization of phenethyl ketone oximes with [Bu4N]Re04 and CF3SO3H and the cyclic imine formation from 0-sulfonyl oximes both proceed by intramolecular S 2-type reaction on the nitrogen atom of the oximes (Scheme 33). ° In contrast, both of the E- and Z-isomers cyclized smoothly and only 8-hydroxyquinoline was obtained regioselectively without forming 6-hydroxy derivatives. These phenomena are not consistent with a nucleophilic substitution reaction, and the cyclization of 0-2,4-dinitrophenyloxime 80a seemed to proceed by another reaction pathway (Scheme 37). To check isomerization of the 0-2,4-dini-trophenyloxime 84, the Z-isomer was treated with NaH and m-cresol. The isomerization of (Z)-84 hardly occurred, but 4-phenylbutan-2-one azine (85) and 4-phenyl-2-butanone (86) were obtained in 27 and 11%... 

FLUOROPHENYL)-4-(4-HYDROXY-4-(3-(TRIFLUORO-METHYL)PHENYL)-l-PIPERIDINYL)-l-BUTANONE MCN-JR-2498 PSICOPERIDOL-R PSYCHOPERIDOL R-2498 TRIFLUPERIDOLO (ITALIAN) TRIPERIDOL... 

SYNS 2-BUTANONE, 4-(4-HYDROXY-3-xMETHOXY-PHENYL)- GINGERONE 4-(4-HYDROXY-3-METHOXYPHENYL)-2-BUTANONE (4-HYDROXY-3-METHOXYPHENYL)ETHYL METHYL KETONE 3-METHOXY-4-HYDROXY-BENZYLACETONE (0)-PARADOL ZINGERONE ZINGIBERONE... 

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