IE43510B1 - Nitrile and production of nitriles - Google Patents

Nitrile and production of nitriles

Info

Publication number
IE43510B1
IE43510B1 IE1737/76A IE173776A IE43510B1 IE 43510 B1 IE43510 B1 IE 43510B1 IE 1737/76 A IE1737/76 A IE 1737/76A IE 173776 A IE173776 A IE 173776A IE 43510 B1 IE43510 B1 IE 43510B1
Authority
IE
Ireland
Prior art keywords
chg
compound
dimethyl
nitrile
hydroxy
Prior art date
Application number
IE1737/76A
Other versions
IE43510L (en
Original Assignee
Anic Spa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Anic Spa filed Critical Anic Spa
Publication of IE43510L publication Critical patent/IE43510L/en
Publication of IE43510B1 publication Critical patent/IE43510B1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)

Abstract

3,7-Dimethyl-2-octenenitrile of the formula (II), a novel nitrile compound having a perfuming action, is obtained by a hydrogenation process from 3,7-dimethyl-3-hydroxy-6-octenenitrile, which gives the corresponding octanonitrile: from the latter, the compound of the formula (I) can be obtained by dehydration. The octanonitrile intermediate also possesses a characteristic pleasant odour.

Description

is invention relates to two nitriles, one of which is novel, and to their sduction. aspect of the present invention provides 3,7-dimethyl-3-hydroxy-octane-ltrile having the following formula:8 7 6 5 4 3 2 1 CHg-CH-CHg-CHg-CHg-C(OH)——CHg-CN (I) ch3 ch3 ter aspects of the present invention provide a process for producing compound nd a process for producing 3,7-dimethyl-oct-2-ene-l-nitrile having the lowing formula:8 7 6 5 4 3 2 1 CH,-CH—-CH,--CH,-CH,-C=CH—CN (11) CHg CHg compounds I and II—and more particularly compound II-—possess a characterically pleasant scent which enables them to be used as perfumes and for the nulation, in conjunction with other known compounds, of perfumed mixtures which be used for soaps, cosmetics and deodorants. In this sense, they can replace i advantage, 3,7-dimethyl-octa-2,6-diene-l-nitrile (III): CH-—C=CH—CH,—CH,—C=CH—CN Π ι CHg CHg - 2 43510 which is known as geranonitrile, in comparison.with which they have a sweeter fragrance and an improyed chemical stability.
In this connection, it should be noticed that, whereas geranonitrile, upon treatment for a few days at room temperature with a mixture of 98? HgSO^ and glacial CHjCOOH in the volume proportions of 5 to 25 gives rise, upon addition of water, to a slightly volatile pitchy substance, compound (II), which is saturated at the 6- and 7-positions, remains unaltered.
Another important application of compounds I and II is thfeir use as intermediates in a number of organic syntheses.
Compounds I and II can be produced by using as the starting material, 3,7di methyl-3-hydroxy-oct-6-ene-l-nitri 1e (IV): CH3—C=CH—CH2—CH2—C (OH)—CHg—CN ch3 ci!3 Compound IV can be obtained according to a synthesis disclosed in Patent No. 41921.
Thus compound I can be produced by hydrogenation of compound IV, and compound II can be produced by dehydration of compound I.
The following Examples illustrate the present invention.
EXAMPLE 1 .28 Grams of 3,7-dimethyl-3-hydroxy-oct-6-ene-l-nitrile (IV) in 25 ml hexane, supplemented by 0.52 gram of a catalyst comprising palladium on activated charcoal (containing 5% Pd by weight), were hydrogenated with stirring, in a glass apparatus, at room temperature, and under a hydrogen pressure of 760+100 millimetres of mercury, absolute pressure.
The absorption of the stoichiometric amount of hydrogen to saturate the double bond of compound IV took about one hour.
After this time, the catalyst was filtered off and the solvent was evaporated under vacuum, and 3,7-dimethyl-3-hydroxy-octane-l-nitrile (I) was collected; the conversion and the selectivity with respect to compound I were both over 90%.
On subsequent distillation in vaouo with a Vigreux column, a product was obtained - 3 £3Si.O rich, has a purity of ahout 98% and a boiling point of 83?C-84°C under an isolute pressure of 0,3 mmHg, EXAMPLE 2 ie compound I was obtained using the same ratio between the reactants as in «ample 1, but by carrying out the hydrogenation in a steel autoclave under an litial hydrogen pressure of 8,6 kilograms per square centimetre (gauge). The -ocedures for collecting and purifying the product were yery much the same as ir Example 1.
EXAMPLE 3 Grams of 3,7-dimethyl-3-hydroxy-octane-l-nitrile (I) and 3 grams of basic ielm aluminium oxide were maintained for 1.5 hours at 220°C-23Q°C under a Itrogen stream in a glass flask equipped with, a bubhle condenser which was ioled with water. :ter this stage, the mixture contents of the flask were allowed to cool to room ‘mperature, then the reaction mass was taken up with diethyl ether and filtered, id the solvent was then thoroughly evaporated. ius, 3,7-dimethyl-oct-2-ene-l-nitrile (II) was obtained, which was composed of mixture of the cis- and trans-isomers in a ratio of 45/55 approximately; the ilectivity with respect to compound II was not less than 90%. impound II was obtained at a purity of 98% approx, by subjecting the residue described hereinabove to distillation in vacuo and collecting the product n'ch boiled at 52°C-53°C under an absolute pressure of 0.1 mmHg. e characterization of compounds I and II was effected by IR, NMR and massectrography analyses, e IR spectrum confirmed the presence of the following functional groups: H 3460 cnr? =N (non conj.) 2252 cm-1 for compound (I) -0 of a tert.alcohol 1153 cm’1 —H 3045 cm-1) ΞΝ (conj, at alpha) 2215 cm-1 for compound (II) C (conj.) 1630 cm-1 Ji (stretching) 700 cm-]/ - 4 10 The NMR analysis (solvent CC14, internal standard hexamethyldisoloxane HMDS) indicated the following characteristic signals:-OH -Cr(2) -CH2-(4)J -CH -CH, -CH ) i—(5,6)( 3,23 parts ner million (ppm) 2.42 ppm’' 1.45 pm 1.24 ppm 7 for compound (I) / \ CH3 0.83 ppm =CH 5.03 ppnT’ -CHz-(4) 2.08 ppm -CHg(cis- or trans-)1.98 ppm -CHg(trans - or cis-)1.85 ppm -CH -(6)) 1.50 ppm -CH2-(5)J -CH 1.20 ppm CH, / 3 \ 0.81 PPm_ \h3 for the compound (II) Mass spectrometry confirmed the molecular weights (169 for I and 151 for II) and the respective expected structures.

Claims (3)

  1. 2. 3,7-Dimethyl-3-hydroxy-octane-l-nitrile having the following formula:8 CH
  2. 3. 7 6 5 4 3 2 1 ig—-C|i—“-CHg—-CHg—-CHg·- C (OH)——CHg—CN CHCH(I) . A process for producing the compound claimed in claim 1, which comprises /drogenating 3 s 7-dimethyl-3-hydroxy-oct-6-enenitrile with hydrogen. . A process according to claim 2, substantially as described in the foresing Example 1 or 2. . A process for producing 3,7-dimethyl-oct-2-ene-l-nitrile having the blowing formula:CHg—CH—CHg—CHg—CHg—j: cl, 3 2 1 :=CH—CN CH, (II) rich process comprises dehydrating the compound claimed in claim 1. , A process according to claim 4, substantially as described in the foreting Example 3. , 3,7-Dimethyl-oct-2-ene-l-nitrile whenever produced by a process according ι claim 4 or 5.
IE1737/76A 1975-08-08 1976-08-05 Nitrile and production of nitriles IE43510B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT26221/75A IT1040373B (en) 1975-08-08 1975-08-08 NITRILS AND PROCEDURE FOR THE LORD PREPARATION

Publications (2)

Publication Number Publication Date
IE43510L IE43510L (en) 1977-02-08
IE43510B1 true IE43510B1 (en) 1981-03-11

Family

ID=11218973

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1737/76A IE43510B1 (en) 1975-08-08 1976-08-05 Nitrile and production of nitriles

Country Status (31)

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JP (1) JPS5219623A (en)
AT (1) AT345780B (en)
AU (1) AU499775B2 (en)
BE (1) BE844977A (en)
BG (1) BG24667A3 (en)
BR (1) BR7605212A (en)
CA (1) CA1098915A (en)
CH (1) CH628024A5 (en)
CS (2) CS191998B2 (en)
DD (1) DD125743A5 (en)
DE (1) DE2635545C3 (en)
DK (1) DK355576A (en)
ES (1) ES450918A1 (en)
FR (1) FR2320289A1 (en)
GB (1) GB1523028A (en)
HU (2) HU174410B (en)
IE (1) IE43510B1 (en)
IN (1) IN144716B (en)
IT (1) IT1040373B (en)
LU (1) LU75553A1 (en)
MX (1) MX3857E (en)
NL (1) NL169998C (en)
NO (1) NO142959C (en)
PL (1) PL101728B1 (en)
PT (1) PT65448B (en)
RO (1) RO69916A (en)
SE (1) SE7608868L (en)
SU (1) SU617009A3 (en)
TR (1) TR19097A (en)
YU (1) YU192276A (en)
ZA (1) ZA764471B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5495821A (en) * 1977-12-27 1979-07-28 Cummins Engine Co Inc Method of recirculating part of exhaust gas for reducing pullutant
US4277377A (en) * 1979-03-22 1981-07-07 Bush Boake Allen Limited Perfume compositions containing dimethyl heptenonitriles
US4863631A (en) * 1988-06-24 1989-09-05 International Flavors & Fragrances Inc. Dimethyl substituted alkyl nitriles, perfume and bleach compositions containing same organoleptic uses thereof and process intermediates for producing same
DE3914391A1 (en) * 1989-04-29 1991-01-17 Basf Ag SS, (GAMMA) - UNSATURATED NITRILES, THEIR PRODUCTION AND USE AS A FRAGRANCE
DE10247966A1 (en) 2002-10-15 2004-05-06 Symrise Gmbh & Co. Kg 5,7,7-trimethyloctanenitrile
MX2011002550A (en) * 2008-10-13 2011-04-04 Firmenich & Cie Chemically stable ingredients as lemon odorant.
EP3612620B1 (en) * 2017-04-21 2021-03-03 Symrise AG 4-ethyl-octene-2/3-nitrile as a fragrance

Also Published As

Publication number Publication date
HU174410B (en) 1980-01-28
PT65448A (en) 1976-09-01
TR19097A (en) 1978-05-16
DD125743A5 (en) 1977-05-18
JPS5219623A (en) 1977-02-15
IE43510L (en) 1977-02-08
SE7608868L (en) 1977-03-01
GB1523028A (en) 1978-08-31
HU177537B (en) 1981-11-28
IT1040373B (en) 1979-12-20
ES450918A1 (en) 1977-08-16
DE2635545A1 (en) 1977-02-10
FR2320289A1 (en) 1977-03-04
CS191982B2 (en) 1979-07-31
SU617009A3 (en) 1978-07-25
NL7608847A (en) 1977-02-10
DE2635545C3 (en) 1980-02-28
LU75553A1 (en) 1977-03-25
ATA585476A (en) 1978-02-15
NO142959B (en) 1980-08-11
AU1637976A (en) 1978-02-02
CA1098915A (en) 1981-04-07
NO142959C (en) 1980-11-19
DE2635545B2 (en) 1979-06-13
DK355576A (en) 1977-02-09
RO69916A (en) 1981-04-30
AT345780B (en) 1978-10-10
CS191998B2 (en) 1979-07-31
PT65448B (en) 1978-02-10
FR2320289B1 (en) 1979-08-10
NL169998C (en) 1982-09-16
ZA764471B (en) 1977-07-27
BR7605212A (en) 1977-08-09
CH628024A5 (en) 1982-02-15
YU192276A (en) 1982-10-31
MX3857E (en) 1981-08-24
PL101728B1 (en) 1979-01-31
AU499775B2 (en) 1979-05-03
NO762718L (en) 1977-02-09
BG24667A3 (en) 1978-04-12
IN144716B (en) 1978-06-24
BE844977A (en) 1977-02-07

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