GB740993A - Production of gamma-lactones - Google Patents

Production of gamma-lactones

Info

Publication number
GB740993A
GB740993A GB743453A GB743453A GB740993A GB 740993 A GB740993 A GB 740993A GB 743453 A GB743453 A GB 743453A GB 743453 A GB743453 A GB 743453A GB 740993 A GB740993 A GB 740993A
Authority
GB
United Kingdom
Prior art keywords
aceto
butyl
alkyl
butyrolactone
acetoacetate
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
GB743453A
Inventor
Richard Norman Lacey
Hubert Jowitt
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
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 Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB743453A priority Critical patent/GB740993A/en
Publication of GB740993A publication Critical patent/GB740993A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

Landscapes

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

Abstract

a -Aceto-g -lactones of the formula <FORM:0740993/IV(a)/1> are prepared by reacting tertiary alkyl (C4-C6) esters of acetoacetic acid with epoxides of the formula <FORM:0740993/IV(a)/2> or derivatives (e.g. chlorhydrins) which generate them under the reaction conditions; the process is carried out in an aqueous solution of an alkali metal hydroxide between -10 DEG and +10 DEG C. (preferably -3 DEG C. to +3 DEG C.); in the formul R is hydrogen, alkyl, alkenyl, aryl, aralkyl, alkoxy-alkyl or aryloxy-alkyl. The epoxide or chlorhydrin and the acetoacetic ester may be added to the alkali, or alternatively the latter two may first be reacted to form the sodium derivative of the ester. The two organic reactants may be used in equimolecular proportions or up to 50 per cent excess of one may be taken. The reaction mixture is agitated continuously. The lactone is isolated by neutralization of the reaction mixture with an acid, extraction with a water-immiscible solvent (e.g. toluene), flash distillation to remove water and some of the solvent and tertiary alkanol, and finally fractional distillation. Examples show the production of (1) a -aceto-g -butyrolactone from ethylene oxide and t.-butyl acetoacetate; (2) a -aceto-g -valerolactone from propylene oxide and t.-butyl or t.-amyl acetoacetate; (3) a -aceto - g - ethoxymethyl - g - butyrolactone from glycidyl ethyl ether and t.-butyl acetoacetate; and (4) a -aceto-g -phenyl-g -butyrolactone from styrene oxide and t.-butyl acetoacetate. Other groups specified for R are ethyl, n-propyl, isopropyl, n-butyl, t.-butyl, n-hexyl, methoxymethyl, 2-methoxypropyl, 1-isopropoxyhexyl, phenoxymethyl, 1-phenoxyethyl, o-toloxymethyl, tolyl, xylyl, benzyl, o-methylbenzyl, m-ethylbenzyl, p-isopropylbenzyl, vinyl, allyl, crotyl and 1-pentenyl. The products may be hydrolysed with sulphuric or hydrochloric acid to the corresponding keto-alcohols or keto-chlorides respectively, e.g. 5-hydroxyhexan-2-one (R=methyl) or 5-chloro-pentan-2-one (R=4) which are useful intermediates.
GB743453A 1953-03-18 1953-03-18 Production of gamma-lactones Expired GB740993A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB743453A GB740993A (en) 1953-03-18 1953-03-18 Production of gamma-lactones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB743453A GB740993A (en) 1953-03-18 1953-03-18 Production of gamma-lactones

Publications (1)

Publication Number Publication Date
GB740993A true GB740993A (en) 1955-11-23

Family

ID=9833027

Family Applications (1)

Application Number Title Priority Date Filing Date
GB743453A Expired GB740993A (en) 1953-03-18 1953-03-18 Production of gamma-lactones

Country Status (1)

Country Link
GB (1) GB740993A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0348549A1 (en) * 1988-07-01 1990-01-03 QUANTUM CHEMICAL CORPORATION (a Virginia corp.) Improved process for the preparation of substituted furanones
CN109651318A (en) * 2018-12-19 2019-04-19 万华化学集团股份有限公司 A kind of preparation method of δ-valerolactone

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0348549A1 (en) * 1988-07-01 1990-01-03 QUANTUM CHEMICAL CORPORATION (a Virginia corp.) Improved process for the preparation of substituted furanones
CN109651318A (en) * 2018-12-19 2019-04-19 万华化学集团股份有限公司 A kind of preparation method of δ-valerolactone

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