GB857163A - A process for the preparation of tridecane-1:13-dicarboxylic acid or its ester, suitable for the preparation of exaltone (cyclopentadecanone) - Google Patents

A process for the preparation of tridecane-1:13-dicarboxylic acid or its ester, suitable for the preparation of exaltone (cyclopentadecanone)

Info

Publication number
GB857163A
GB857163A GB1704/58A GB170458A GB857163A GB 857163 A GB857163 A GB 857163A GB 1704/58 A GB1704/58 A GB 1704/58A GB 170458 A GB170458 A GB 170458A GB 857163 A GB857163 A GB 857163A
Authority
GB
United Kingdom
Prior art keywords
acid
ester
semi
tridecane
aldehyde
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
GB1704/58A
Inventor
Bhausaheb Bapusaheb Ghatgey
Ullal Govindraj Nayak
Kamala Kinkar Chakravarti
Sasanka Chandra Bhattacharyya
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.)
Council of Scientific and Industrial Research CSIR
Original Assignee
Council of Scientific and Industrial Research CSIR
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 Council of Scientific and Industrial Research CSIR filed Critical Council of Scientific and Industrial Research CSIR
Publication of GB857163A publication Critical patent/GB857163A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • 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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Tridecane -1 : 13-dicarboxylic acid or its methyl or ethyl ester are prepared by (i) oxidising an ester of the formula CH3 (CH2) CH(OH) CH(OH)-R1-COOAlk with an a , b -glycol rupturing agent which will form aldehyde groups, preferably sodium metaperiodate, to give the semi-aldehyde ester of the formula OHC-R1-COOAlk, in which formula R1 represents -(CH2)11-or-(CH2)13-and Alk represents a methyl or ethyl group, and (ii) converting said semi-aldehyde ester into tridecane-1 : 13-dicarboxylic acid or its methyl or ethyl ester. When R1 = -(CH2)13-, step (ii) may be effected by oxidising the semi-aldehyde ester in acetone solution with aqueous potassium permanganate solution in the presence of an acid, such as acetic acid, to yield a semi-acid ester which on alkaline hydrolysis and acidification yields tridecane-1 : 13-dicarboxylic acid. The semi-aldehyde ester of brassylic acid in which R1 = -(CH2)4- may be oxidised with potassium permanganate to brassylic acid semi-ester which may be saponified to brassylic acid or esterified to diethyl brassylate. The latter can be converted to the diol, dibromide, dinitrile and thus to tridecane-1 : 13-dicarboxylic acid. Alternatively the semi-aldehyde ester may be subjected to the Knoevenagel Reaction with malonic ester or malonic acid, followed by hydrogenation, hydrolysis and decarboxylation to form tridecane-1 : 13-dicarboxylic acid. Alternatively the semi-aldehyde ester may be subjected to the Reformatsky reaction with a haloacetic ester, followed by dehydration, hydrogenation and hydrolysis, to form tridecane-1 : 13-dicarboxylic acid. This product may be esterified to form the dimethyl or diethyl ester. The diethyl ester may be converted to the acyloin by reaction with sodium in xylene and the product reduced in alcoholic solution with zinc and hydrogen chloride to give cyclopent-decanone (exaltone). The dihydroxy fatty acid ester starting material is obtained by oxidation of an unsaturated acid CH3 (CH2)7 CH=CH. R1 COOH, for example, with hydrogen peroxide and acetic or formic acid in the presence of an acid catalyst, followed by esterification. The unsaturated fatty acids utilised are erucic acid obtained from mustard oil and nervonic acid synthesised from erucic acid by a known process. For example erucic acid may be reduced to the alcohol and converted to the bromide which is reacted with malonic ester and the product hydrolysed and decarboxylated to give nervonic acid.
GB1704/58A 1957-01-19 1958-01-17 A process for the preparation of tridecane-1:13-dicarboxylic acid or its ester, suitable for the preparation of exaltone (cyclopentadecanone) Expired GB857163A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IN857163X 1957-01-19

Publications (1)

Publication Number Publication Date
GB857163A true GB857163A (en) 1960-12-29

Family

ID=11076639

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1704/58A Expired GB857163A (en) 1957-01-19 1958-01-17 A process for the preparation of tridecane-1:13-dicarboxylic acid or its ester, suitable for the preparation of exaltone (cyclopentadecanone)

Country Status (1)

Country Link
GB (1) GB857163A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0285372A2 (en) * 1987-03-31 1988-10-05 Nippon Mining Company Limited Method for purifying macrocyclic ketones
WO2007143873A1 (en) * 2006-06-15 2007-12-21 Givaudan Sa Fragrance compounds

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0285372A2 (en) * 1987-03-31 1988-10-05 Nippon Mining Company Limited Method for purifying macrocyclic ketones
EP0285372A3 (en) * 1987-03-31 1990-04-25 Nippon Mining Company Limited Method for purifying macrocyclic ketones
WO2007143873A1 (en) * 2006-06-15 2007-12-21 Givaudan Sa Fragrance compounds
JP2009540066A (en) * 2006-06-15 2009-11-19 ジボダン エス エー Fragrance compounds
US8575386B2 (en) 2006-06-15 2013-11-05 Givaudan S.A. Fragrance compounds
US9057041B2 (en) 2006-06-15 2015-06-16 Givaudan, S.A. Fragrance compounds
US9447364B2 (en) 2006-06-15 2016-09-20 Givaudan S.A. Fragrance compounds
US9585362B2 (en) 2006-06-15 2017-03-07 Givaudan S.A. Fragrance compounds

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