GB739022A - Improvements in or relating to the preparation of heterocyclic compounds - Google Patents

Improvements in or relating to the preparation of heterocyclic compounds

Info

Publication number
GB739022A
GB739022A GB24131/53A GB2413153A GB739022A GB 739022 A GB739022 A GB 739022A GB 24131/53 A GB24131/53 A GB 24131/53A GB 2413153 A GB2413153 A GB 2413153A GB 739022 A GB739022 A GB 739022A
Authority
GB
United Kingdom
Prior art keywords
methyl
glycol
dioxolanes
reacting
preparation
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
GB24131/53A
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.)
Olin Corp
Original Assignee
Olin 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 Olin Corp filed Critical Olin Corp
Publication of GB739022A publication Critical patent/GB739022A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,3-Dioxolanes are prepared by reacting a vicinal glycol with a carbonyl compound in the presence of an acidic cation exchange resin at an elevated temperature, e.g. at 50 DEG to 150 DEG C. An excess of the glycol is preferably employed, and the amount of resin in the contacting zone may be about 2 to 10 per cent of the weight of the reacting mixture. A solvent such as glycol, benzene, toluene or petroleum ether may be present. Sulphonated resins are preferably used as the cation exchange resin, but the use of resins containing carboxylic, phenolic or phosphonic polar groups also is referred to. Examples describe the preparation of (1) 1,3-dioxolane, and the following substituted 1,3-dioxolanes, namely, (2) 2-propyl-, (3) 2-(1-ethylpentyl)-, (4) 2-amyl-, (5) 2-isopropyl-, (6) 2-methyl-2-isopropyl-, (7) 2,2-pentamethylene-, (8) 2-furyl-, (9) 2-(21-methoxyethyl)-, (10) 2-(1-ethylpentenyl-1)-, (11) 2-chloromethyl-, (13) 2-methyl-2-carbethoxymethyl-, (14) 4-methyl-, (15) 4,5-dimethyl-, (16) 2-(1-ethylpropyl)-4-methyl-, and (17) 2-propyl-4-methyl-1,3-dioxolanes, and also (12) the bis-compound obtained by reacting ethylene glycol with glyoxal.
GB24131/53A 1952-09-03 1953-09-01 Improvements in or relating to the preparation of heterocyclic compounds Expired GB739022A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US739022XA 1952-09-03 1952-09-03

Publications (1)

Publication Number Publication Date
GB739022A true GB739022A (en) 1955-10-26

Family

ID=22116487

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24131/53A Expired GB739022A (en) 1952-09-03 1953-09-01 Improvements in or relating to the preparation of heterocyclic compounds

Country Status (1)

Country Link
GB (1) GB739022A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198393A (en) * 1977-08-24 1980-04-15 International Flavors & Fragrances Inc. Cyclic acetals of 2-methyl-2-pentenal and food flavor uses thereof
US4289700A (en) * 1977-08-24 1981-09-15 International Flavors & Fragrances Inc. Cyclic acetals of 2-methyl-2-pentenal and food flavor uses thereof
US4418231A (en) 1981-08-07 1983-11-29 Ppg Industries, Inc. Corrosion inhibited solvent compositions
US4466903A (en) * 1981-08-07 1984-08-21 Ppg Industries, Inc. Unsaturated 1,3-dioxolane stabilized with aliphatic aldehyde hydrazone
US4532338A (en) * 1983-07-13 1985-07-30 Ppg Industries, Inc. Process for producing 2-halomethyl-1,3-cyclic acetal

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198393A (en) * 1977-08-24 1980-04-15 International Flavors & Fragrances Inc. Cyclic acetals of 2-methyl-2-pentenal and food flavor uses thereof
US4289700A (en) * 1977-08-24 1981-09-15 International Flavors & Fragrances Inc. Cyclic acetals of 2-methyl-2-pentenal and food flavor uses thereof
US4418231A (en) 1981-08-07 1983-11-29 Ppg Industries, Inc. Corrosion inhibited solvent compositions
US4466903A (en) * 1981-08-07 1984-08-21 Ppg Industries, Inc. Unsaturated 1,3-dioxolane stabilized with aliphatic aldehyde hydrazone
US4532338A (en) * 1983-07-13 1985-07-30 Ppg Industries, Inc. Process for producing 2-halomethyl-1,3-cyclic acetal

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