- METHOD FOR PRODUCING N,N-DIALKYLHOMOFARNESIC ACID AMIDE
-
Provided are: a method for producing N,N-dialkylhomofarnesic acid amide, which is a precursor of (±)-3a,6,6,9a-tetramethyldodecahydronaphtho[2.1-b]furan that is useful as a fragrance, at a high recovery rate of a raw material, at a high purity and at a high yield; and a method for producing (±)-3a,6,6,9a-tetramethyldodecahydronaphtho[2.1-b]furan. It is a method for producing N,N-dialkylhomofarnesic acid amide, said method including reacting nerolidol with N,N-dialkylformamide dimethyl acetal under the conditions that the N,N-dialkylformamide dimethyl acetal can be refluxed, wherein the molar ratio of the N,N-dialkylformamide dimethyl acetal to the nerolidol is in a range of 1.5 to 3.
- -
-
Paragraph 0081; 0084; 0085
(2015/09/23)
-
- PROCESS FOR PRODUCING (±)-3a,6,6,9a-TETRAMETHYL DODECAHYDRONAPHTHO[2,1-b]FURANS
-
The present invention relates to a process for producing (±)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,l-b]furans from crude (±)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,l-b]furans obtained by subjecting (±)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,l-b]furan-2(lH)-ones which are produced by cyclizing a homofarnesylic acid amide or a monocyclohomofarnesylic acid amide in the presence of an acid agent and then hydrolyzing the cyclized product, to reduction reaction and then to cyclization reaction, said process including (i) an alkali treatment step in which the crude (±)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,l-b]furans are heated in the presence of an alcohol and a metal hydroxide; and (ii) a washing treatment step in which the crude (±)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,l-b]furans are washed with an aqueous acid solution. The thus obtained (±)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,l-b]furans have a less off-odor and hardly suffer from deterioration of their smell during storage.
- -
-
Page/Page column 15
(2010/09/03)
-
- PROCESS FOR PRODUCTION OF (±)-3a,6,6,9a TETRAMETHYLDECAHYDRONAPHTHO[2,1-b]FURAN-2(1H)-ONE
-
The present invention relates to industrially useful production processes in which (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones and further (±)-3a,6,6,9a-tetramethyldo decahydronapbtho[2,1-b]furans are produced from raw materials which are readily available at low costs, through short steps and in a simple manner. The process for producing (±)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones represented by the general formula (III): which includes the steps of cyclizing a homofarnesylic acid amide represented by the general formula (I): wherein R1 and R2 are each independently an alkyl group having 1 to 4 carbon atoms; and wavy lines each represents a carbon-to-carbon single bond having a cis or trans structure, and/or a monocyclohomofarnesylic acid amide represented by the general formula (II): wherein R1 and R2 and wavy lines are the same as defined above; and dotted lines represent that a carbon-to-carbon double bond is present at any of positions represented by the dotted lines, in the presence off an acid agent; and subjecting the cyclized product to hydrolysis.
- -
-
Page/Page column 10; 12
(2009/05/29)
-
- Formal synthesis of (±)-Ambrox
-
The immediate precursor of (±)-Ambrox 1 has been conveniently prepared in a seven-step sequence starting from the readily available methyl 2-oxo-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 2, in turn derived by stannic chloride-mediated cyclization of methyl 3-oxo-5-(2,6,6-trimethylcyclohexen-1-yl)pentanoate.
- Barco, Achille,Benetti, Simonetta,Bianchi, Anna,Casolari, Alberto,Guarneri, Mario,Pollini, Gian P.
-
p. 8333 - 8338
(2007/10/02)
-
- Ambergris compounds from labdanolic acid
-
Labdanolic acid (Cistus ladaniferus) is transformed into derivatives with amber odor. The strategy used allowed a process in which the oxidative decarboxylation reaction was carried out with the hydroxyl group protected.
- Urones,Basabe,Marcos,Gonzalez,Jimenez,Sexmero,Lithgow
-
p. 9991 - 9998
(2007/10/02)
-
- A formal synthesis of (±)-Ambrox
-
Bicyclic diol 6, a direct precursor of (±)-Ambrox ((±)-7), has been synthesised in four steps (35% yield) from the known bicyclic enone 2.
- Snowden,Linder
-
p. 4119 - 4120
(2007/10/02)
-
- Configuration-Odor Relationship in 5β-Ambrox
-
The four possible A/B cis-fused diastereomers of Ambrox have been synthesized and their configurations and conformations established by X-ray and NMR analysis.Only 5β-ambrox (=1,2,3a,4,5,5aβ,6,7,8,9,9a,9bα-dodecahydro-3aβ,6,6,9aβ-tetramethylnaphthofuran; 5) has an odor quality comparable to Ambrox.The 1,3-synperiplanar/diaxial conformation of the substituents at C(8) (=C(3a)) and C(10) (=C(9a)) has thus been confirmed to be a compulsory structure element for the particular odor.
- Escher, Sina,Giersch, Wolfgang,Niclass, Yvan,Bernardinelli, Gerald,Ohloff, Guenther
-
p. 1935 - 1947
(2007/10/02)
-
- Preparation of alkylated dodechydronaphto[2,1-b]furans
-
Alkylated dodecahydronaphtho[2,1-b]furans of the general formula I STR1 where R1 and R2 are identical and each is hydrogen or methyl are prepared by reacting alkylated 2-hydroxydecahydronaphthalene-1-ethanol of the formula II STR2 where R1 and R2 are as defined above, with a sulfonyl chloride in the presence of basic catalysts by performing the cyclization in the presence of concentrated aqueous alkali metal hydroxides and a phase transfer catalyst, preferably a tetra-substituted ammonium or phosphonium salt, the sulfonyl chloride used preferably comprising a sulfonyl chloride of the general formula III where R3 is C1 -C3 -alkyl or phenyl which may be substituted in the para position by methyl, chlorine, bromine or nitro.
- -
-
-
- Triterpenoid Total Synthesis, I: Synthesis of Ambrein and Ambrox
-
The first total synthesis of (+)-ambrein (1), a triterpene alcohol isolated from ambergris, was achieved.Both the enantiomers of ambrox (2) were also synthesized.
- Mori, Kenji,Tamura, Hiroshi
-
p. 361 - 368
(2007/10/02)
-
- 110. The Synthesis of Racemic Ambrox
-
(+/-)-Ambrox (10), the racemic form of (-)-Ambrox, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps.The racemic ether retains the characteristic scent of fine-quality ambergris, and the odor threshold of the racemate and the (-)-enantiomer prepared from natural sclareol found to be essentially identical.
- Buechi, George,Wueest, Hans
-
p. 996 - 1000
(2007/10/02)
-
- Process for the production of isosolanone and solanone, intermediates useful in said process and organoleptic uses of said intermediates
-
Described is a novel genus of compounds defined according to the structure: STR1 wherein Z represents hydrogen, MgX and the moiety having the structure: STR2 and X represents chlor, bromo, or iodo; as well as 5-isopropyl-8-methyl-5,8-nonadien-2-one; uses of same as intermediates in a process for producing isosolanone and solanone; and organoleptic uses of 5-isopropyl-8-methyl-5,8-nonadien-2-one and 2,6-dimethyl-5-methylene-1-hepten-4-ol. The novel process of our invention involved the steps of: (i) formation of the compound having the structure: STR3 by means of reacting 3-methyl-2-methylenebutanal with the compound having the structure: STR4 (ii) acid hydrolysis of the resulting compound in order to form 2,6-dimethyl-5-methylene-1-heptene-4-ol; (iii) reaction of 2,6-dimethyl-5-methylene-1-hepten-4-ol with methyl aceto acetate in order to form 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate or, directly, 5-isopropyl-8-methyl-5,8-nonadiene-2-one; (iv) reacting 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate in the presence of an appropriate catalyst to form the 5-isopropyl-8-methyl-5,8-nonadiene-2-one; and (v) isomerizing the 5-isopropyl-8-methyl-5,8-nonadien-2-one in order to form a mixture of solanone and the isosolanone or 5-isopropyl-8-methyl-5,8-nonadiene-2-one.
- -
-
-