GB1209903A - Long chain hydrocarbon esters and acids and process for their production - Google Patents

Long chain hydrocarbon esters and acids and process for their production

Info

Publication number
GB1209903A
GB1209903A GB5585868A GB5585868A GB1209903A GB 1209903 A GB1209903 A GB 1209903A GB 5585868 A GB5585868 A GB 5585868A GB 5585868 A GB5585868 A GB 5585868A GB 1209903 A GB1209903 A GB 1209903A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydrogen
double bond
acids
group
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5585868A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zoecon Corp
Original Assignee
Zoecon Corp
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 Zoecon Corp filed Critical Zoecon Corp
Publication of GB1209903A publication Critical patent/GB1209903A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • C07C31/44—Halogenated alcohols containing saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,209,903. Long chain hydrocarbon acids and esters thereof. ZOECON CORP. 30 Aug., 1967 [15 Sept., 1966; 28 Oct., 1966; 7 Nov., 1966; 24 Feb., 1967], No. 55858/68. Heading C2C. [Also in Division A5] The invention comprises compounds of the. formula in which R<SP>5</SP> is hydrogen or C 1-6 alkyl, each of R<SP>1-4</SP> is a C 1-6 alkyl group, Z<SP>2</SP> is H or OH, Z<SP>3</SP> is H, OH, Cl, Br, F or C 1-6 alkoxy or when taken together with Z<SP>2</SP> represents a carbon-carbon double bond, -O- -CH 2 - -CCl 2 - or -CF 2 -, Z<SP>6</SP> is H, OH, Br, Cl or F, Z<SP>7</SP> is H, OH, Br, Cl, F or C 1-6 alkoxy or, when taken together with Z<SP>6</SP> represents a carbon-carbon double bond, -O-, -CH 2 -, -CCl 2 - or -CF 2 -, Z<SP>10</SP> is H, OH, Br, Cl or F and Z<SP>11</SP> is H, OH, Br, Cl, F or C 1-6 alkoxy or when taken together with Z<SP>10</SP> represents a carbon-carbon double bond, -O-, -CH 2 -, -CCl 2 - or -CF 2 -, the metal salts of the acids and the carboxylic esters, tetrahydropyranyl ethers and tetrahydrofuranyl ethers of compounds containing OH groups, provided that (1) when Z<SP>3</SP> is H, then Z<SP>2</SP> is H, when Z' is H, then Z<SP>6</SP> is H, when Z<SP>11</SP> is H, then Z<SP>10</SP> is H, (2) when each of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is methyl, Z<SP>3</SP> together with Z<SP>2</SP> and Z<SP>7</SP> together with Z 6 are double bonds and Z<SP>11</SP> together with Z<SP>10</SP> is -O-, then R<SP>5</SP> is not hydrogen or methyl, (3) when R<SP>1</SP> is methyl, R<SP>2</SP> is ethyl, one of R<SP>3</SP> or R<SP>4</SP> is methyl and the other is ethyl, Z<SP>3</SP> together with Z<SP>2</SP> and Z<SP>7</SP> together with Z<SP>6</SP> are double bonds and Z<SP>11</SP> together with Z<SP>10</SP> is -O-, then R<SP>5</SP> is not methyl, (4) when each of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is methyl Z<SP>3</SP> together with Z<SP>2</SP> and Z<SP>11</SP> together with. Z<SP>10</SP> are double bonds and Z<SP>7</SP> together with Z<SP>6</SP> is -O-, then R<SP>5</SP> is not hydrogen or methyl, (5) when each of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is methyl, Z<SP>7</SP> together with Z<SP>6</SP> and Z<SP>11</SP> together with Z<SP>10</SP> are double bonds then Z<SP>3</SP> is not OH or, together with Z<SP>2</SP>, -O-, (6) when each of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is methyl, Z' is hydrogen, Z<SP>11</SP> is hydrogen or, together with Z<SP>10</SP>, a double bond, then Z<SP>3</SP> is not OH, (7) when R<SP>1</SP> is m-butyl, each of R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is methyl and Z<SP>7</SP> and. Z<SP>11</SP> are hydrogen, then Z<SP>3</SP> is not hydroxy, (8) when each of R<SP>1</SP> and R<SP>2</SP> is methyl, one of R<SP>3</SP> or R<SP>4</SP> is methyl and the other is 4-methylpentyl; Z<SP>11</SP> is hydrogen and Z<SP>7</SP> together with Z<SP>6</SP> is a double bond, then Z<SP>3</SP> is not OH or halogen, (9) when R<SP>1</SP> is ethyl, Z<SP>3</SP> together with Z<SP>2</SP>, Z<SP>7</SP> together with Z<SP>6</SP> and Z<SP>11</SP> together with Z<SP>10</SP> are all double bonds, then one of R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is not methyl, (10) when one of R<SP>3</SP> or R<SP>4</SP> is methyl, Z<SP>3</SP> is hydrogen or, together with Z<SP>2</SP>, a double bond, Z<SP>7</SP> is hydrogen or, together with Z<SP>6</SP>, a double bond and Z<SP>11</SP> is hydrogen or, together with Z<SP>10</SP>, a double bond, then one of R<SP>1</SP> or R<SP>2</SP> is not methyl, and (11) when Z<SP>3</SP> together with Z<SP>2</SP> is a double bond, Z<SP>6</SP> and Z<SP>10</SP> are hydrogen and Z<SP>7</SP> or Z<SP>11</SP> are Cl and R<SP>5</SP> is alkyl, then one of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> is not methyl; and a process for preparing acids and esters of the formula where R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP>, R<SP>5</SP>, Z<SP>6</SP>, Z<SP>7</SP>, Z<SP>10</SP> and Z<SP>11</SP> are as defined above, excepting provisos (2) to (11), comprising reacting a ketone of the formula with (A) a carbalkoxymethylphosphonate in-the presence of an alkali metal anhydride, or (B) a cyanomethylphosphonate followed by hydrolysis and/or esterification of the terminal cyano group or, optionally, hydrolysis of the terminal ester group. The Z<SP>2</SP>-Z<SP>3</SP> double bond in the above product and any Z<SP>6</SP>-Z<SP>7</SP> or Z<SP>10</SP>-Z<SP>11</SP> double bond in the acid, ester or starting ketone may be subjected to various reactions to introduce the alternative values of the groups Z, e.g. hydrogenation, epoxidation (using m-chloroperbenzoic acid), addition of fused -CH 2 - group (using CH 2 I 2 and a Zn/Cu couple), addition of fused -CF 2 - group (using trimethyltrifluoromethyl tin in the presence of NaI), addition of fused -CCl 2 - group (using phenyldichlorobromo mercury), hydration (using aqueous formic acid or H 2 SO 4 ), halogenation or hydrohalogenation. In addition, the fused -CH 2 - group may be selectively introduced in the 2,3-position by reaction with dimethylsulphoxonium methylide base in dimethylsulphoxide and the fused -O- group may be selectively introduced in the 2,3-position by using H 2 O 2 in an aqueous alkali medium. Other derivatives are obtained by, e.g., reduction of the epoxide to give the mono-hydroxy compounds, cleavage of the epoxide ring using HClO 4 to give the vic-dihydroxy compounds and treatment of the unsaturated compounds with N-Br- or N-Cl-succinimide in an aqueous solvent to give the vic-Cl or Br-hydroxy compounds. The ethers and esters of compounds containing -OH groups are made by conventional etherification and esterification processes. The C 1-6 alkoxy derivatives can also be prepared by conducting any of the above processes yielding -OH compounds in the presence of a C 1-6 alkanol. Examples describe the preparation of a large number of acids and esters, most of which are derivatives of 3,7,11-trimethyldodeca- 2,6,10-trienoic, 3,7,11-trimethyltrideca-2,6,10- trienoic and 3,11 - dimethyl - 7 - ethyltrideca - 2,6,10-trienoic acids. The acids and esters are arthropod maturation inhibitors (see Division A5). In preparations 1-3, the synthesis of some of the starting ketones is described, including the hydrogenation of 6,10-dimethyldodeca-5,9-dien- 2-one to a mixture of 6,10-dimethyldodeca- 5 - en - 2 - one, 6,10 - dimethyldodeca - 9 - en - 2 - one and 6,10-dimethyldodecan-2-one.
GB5585868A 1966-09-15 1967-08-30 Long chain hydrocarbon esters and acids and process for their production Expired GB1209903A (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US57949066A 1966-09-15 1966-09-15
US59019566A 1966-10-28 1966-10-28
US59232466A 1966-11-07 1966-11-07
US59466466A 1966-11-16 1966-11-16
US60556666A 1966-12-29 1966-12-29
US60557866A 1966-12-29 1966-12-29
US61833967A 1967-02-24 1967-02-24
US61832167A 1967-02-24 1967-02-24
US61835167A 1967-12-24 1967-12-24

Publications (1)

Publication Number Publication Date
GB1209903A true GB1209903A (en) 1970-10-21

Family

ID=27578872

Family Applications (8)

Application Number Title Priority Date Filing Date
GB5586068A Expired GB1209905A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon amides and process for their production
GB5585968A Expired GB1209904A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon alcohols and esters and ethers and process for their production
GB1716770A Expired GB1209908A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon alcohols
GB3960167A Expired GB1209902A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon phosphonates and processes for their preparation
GB3300469A Expired GB1209906A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon halides and process for their production
GB2183870A Expired GB1209909A (en) 1966-09-15 1967-08-30 A long chain hydrocarbon ketone
GB5585868A Expired GB1209903A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon esters and acids and process for their production
GB3314669A Expired GB1209907A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon amines and process for their production

Family Applications Before (6)

Application Number Title Priority Date Filing Date
GB5586068A Expired GB1209905A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon amides and process for their production
GB5585968A Expired GB1209904A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon alcohols and esters and ethers and process for their production
GB1716770A Expired GB1209908A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon alcohols
GB3960167A Expired GB1209902A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon phosphonates and processes for their preparation
GB3300469A Expired GB1209906A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon halides and process for their production
GB2183870A Expired GB1209909A (en) 1966-09-15 1967-08-30 A long chain hydrocarbon ketone

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB3314669A Expired GB1209907A (en) 1966-09-15 1967-08-30 Long chain hydrocarbon amines and process for their production

Country Status (5)

Country Link
CH (1) CH494728A (en)
DE (2) DE1793729A1 (en)
FR (1) FR1551052A (en)
GB (8) GB1209905A (en)
NL (1) NL6712568A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1648870A (en) * 1969-07-09 1971-12-23 Fmc Corporation Method of controlling insects and compostion therefor
CH569684A5 (en) * 1972-03-10 1975-11-28 Givaudan & Cie Sa
JPS52131507A (en) * 1976-04-24 1977-11-04 Sankyo Co Ltd Polyprenyl derivatives
CH625676A5 (en) * 1977-07-19 1981-10-15 Ciba Geigy Ag
US4230726A (en) * 1979-06-29 1980-10-28 The United States Of America As Represented By The Secretary Of Agriculture Control of parasitic mites with alkyl amines
PH16234A (en) * 1979-08-14 1983-08-11 Eisai Co Ltd Polyphenylcarboxylic acid amides
JPS57192342A (en) * 1981-05-18 1982-11-26 Nisshin Flour Milling Co Ltd Isoprenylamine derivative
CN113999096B (en) * 2021-11-29 2023-05-30 万华化学集团股份有限公司 Method for synthesizing 6-methyl-5-octene-2-ketone by condensation hydrogenation

Also Published As

Publication number Publication date
GB1209902A (en) 1970-10-21
GB1209906A (en) 1970-10-21
NL6712568A (en) 1968-03-18
DE1618946A1 (en) 1972-06-08
GB1209905A (en) 1970-10-21
GB1209908A (en) 1970-10-21
DE1793729A1 (en) 1973-04-26
FR1551052A (en) 1968-11-18
GB1209907A (en) 1970-10-21
GB1209904A (en) 1970-10-21
GB1209909A (en) 1970-10-21
CH494728A (en) 1970-08-15

Similar Documents

Publication Publication Date Title
Gilman et al. Relative Reactivities of Organometallic Compounds of the Alkaline Earth Group1
GB1209903A (en) Long chain hydrocarbon esters and acids and process for their production
GB1264592A (en)
GB1495064A (en) Trimethylheptadiene derivatives and the manufacture of lavandulol and its esters therefrom
IT1012690B (en) PROCEDURE FOR THE PRODUCTION OF TER-ALKYL ETHERS
GB1130113A (en) Process for the production of bis(aminoalkyl)ethers
CH614217A5 (en) Process for the preparation of 1,3,5(10)-8alpha-oestratrienes
US2942014A (en) Oxidative coupling process
GB1514076A (en) Carotenoid and process for the manufacture thereof
GB1182212A (en) Polyenic Alcohols, Aldehydes and Acids
US2866813A (en) Aldehyde diacylates and process for producing the same
GB1399330A (en) Process for the production of cycloalkenyl compounds
Van Es et al. Mixed carboxylic acid anhydrides: V. Synthesis of alkyl formates
GB1517865A (en) Production of organic phosphorus compounds containing carboxylic groups
GB1209398A (en) Oxygenated decalin derivatives
GB1514836A (en) Production of 2-hydroxynaphthalene-3-carboxylic acid
US3839461A (en) Process for producing organic hydroperoxides
ES345289A1 (en) Process for the preparation of intermediates for the synthesis of steroids
GB1109133A (en) Dihydropyran ethers and unsaturated aliphatic ketoethers
GB1366663A (en) Process for the preparation of cyclopenta /f/ /1/ benzopyrans and 1h-naphto/2 1-6/ pyrans
US3449408A (en) Preparation of esters by carbonylation of alcohols
GB1257431A (en)
GB1438100A (en) Cyclohexane derivatives and their use as odorants
GB1140939A (en) Process for producing an ester
GB791177A (en) Novel esters and a process for the manufacture thereof

Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees