GB744187A - Unsaturated aldehydes and derivatives thereof - Google Patents

Unsaturated aldehydes and derivatives thereof

Info

Publication number
GB744187A
GB744187A GB1739853A GB1739853A GB744187A GB 744187 A GB744187 A GB 744187A GB 1739853 A GB1739853 A GB 1739853A GB 1739853 A GB1739853 A GB 1739853A GB 744187 A GB744187 A GB 744187A
Authority
GB
United Kingdom
Prior art keywords
acrolein
nitro
give
acetaldehyde
bromo
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
GB1739853A
Inventor
Gino Carrara
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.)
Gruppo Lepetit SpA
Original Assignee
Lepetit 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 Lepetit SpA filed Critical Lepetit SpA
Priority to GB1739853A priority Critical patent/GB744187A/en
Publication of GB744187A publication Critical patent/GB744187A/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
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • 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
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0744187/IV(a)/1> where X is sulphur or oxygen, R is hydrogen, halogen or a nitro group and R1 and R2 may be the same and be an alkoxy or aliphatic acyloxy group of 1-6 carbon atoms, or may be different and be a hydroxy group and the salt of a sulphonic group or R1 and R2 together may be an oxygen atom. The aldehydes of the above general formula in which R1 and R2 together are an oxygen atom are made by condensing an aldehyde of the formula <FORM:0744187/IV(a)/2> with acetaldehyde at a temperature below 20-25 DEG C. in the presence of an alkaline condensation catalyst, e.g. an alkali metal hydroxide dissolved in a lower aliphatic alcohol, refluxing the resulting mixture with an aliphatic carboxylic anhydride of 1-6 carbon atoms, adding mineral acid such as hydrochloric acid and brominating the product in the presence of a solvent. The aldehydes may be converted to the corresponding products in which R1 is hydroxyl and R2 is the salt of a sulphonic acid group, or where R1 and R2 are alkoxyl or acyloxy groups of 1-6 carbon atoms, by reaction with aqueous alkali metal bisulphite or with a lower aliphatic alcohol or lower aliphatic acid anhydride respectively. In examples: (1) 5-nitro - 2 - thiophenealdehyde is reacted with acetaldehyde in the presence of a solution of potassium hydroxide in methyl alcohol, the reaction product is refluxed with acetic anhydride, aqueous hydrochloric acid is added and refluxing is continued to give a -(5-nitro-2-thienyl)-acrolein, which is brominated with a solution of bromine in acetic acid to give a -bromo-b -(5-nitro-2-thienyl)-acrolein, which is then converted into its bisulphite compound by reaction with sodium bisulphite; (2) 5-nitro-2-furaldehyde is reacted with acetaldehyde as in (1) and the resulting b -(5-nitro-2-furyl) acrolein is brominated to give a -bromo-b -(5-nitro-2-furyl) acrolein which is converted into its diethyl acetal; (3) 5-chloro-2-thiophenaldehyde is reacted with acetaldehyde as in (1) and the resulting 5-chloro-2-thiopheneacrolein is brominated to give a - bromo - b - (5 - chloro - 2-thienyl) acrolein which is treated with acetic anhydride to give a -bromo-b -(5-chloro-2-thienyl) acrolein diacetate; and (4) furaldehyde is condensed with acetaldehyde and the resulting b - (2 - furyl) acrolein is brominated to give a -bromo-b -(2-furyl)-acrolein.
GB1739853A 1953-06-23 1953-06-23 Unsaturated aldehydes and derivatives thereof Expired GB744187A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1739853A GB744187A (en) 1953-06-23 1953-06-23 Unsaturated aldehydes and derivatives thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1739853A GB744187A (en) 1953-06-23 1953-06-23 Unsaturated aldehydes and derivatives thereof

Publications (1)

Publication Number Publication Date
GB744187A true GB744187A (en) 1956-02-01

Family

ID=10094497

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1739853A Expired GB744187A (en) 1953-06-23 1953-06-23 Unsaturated aldehydes and derivatives thereof

Country Status (1)

Country Link
GB (1) GB744187A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013034A1 (en) * 1978-12-21 1980-07-09 Rütgerswerke Aktiengesellschaft Process for the preparation of beta-(5-nitro-2-furyl)-acrolein

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013034A1 (en) * 1978-12-21 1980-07-09 Rütgerswerke Aktiengesellschaft Process for the preparation of beta-(5-nitro-2-furyl)-acrolein

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