GB715846A - Manufacture of 4-hydroxycoumarin derivatives - Google Patents

Manufacture of 4-hydroxycoumarin derivatives

Info

Publication number
GB715846A
GB715846A GB5800/52A GB580052A GB715846A GB 715846 A GB715846 A GB 715846A GB 5800/52 A GB5800/52 A GB 5800/52A GB 580052 A GB580052 A GB 580052A GB 715846 A GB715846 A GB 715846A
Authority
GB
United Kingdom
Prior art keywords
hydroxycoumarin
per cent
benzalacetone
tributylamine
aniline
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
GB5800/52A
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.)
S B PENICK AND Co
Original Assignee
S B PENICK AND Co
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 S B PENICK AND Co filed Critical S B PENICK AND Co
Publication of GB715846A publication Critical patent/GB715846A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
    • C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
    • C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring

Landscapes

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

Abstract

3 - (a - Phenyl - b - acetylethyl) - 4 - hydroxycoumarin is prepared by condensing 4-hydroxycoumarin with benzalacetone dispersed in water containing ammonia or an organic amine in an amount sufficient to give at least 50 per cent of the theoretical yield. Suitably, the amine is present in an amount of up to 5, 15 or 50 moles. per 100 moles of 4-hydroxycoumarin. Specified organic amines are pyridine, aniline, triethylamine, tributylamine, triethanolamine, piperidine, diethylamine, diethanolamine and monoethanolamine. The product obtained using up to 15 mole per cent of catalyst is usually a solid which is isolated by refluxing in a hydrocarbon or chlorinated hydrocarbon solvent, e.g. benzene, cooling, separating the solid material, filtering, dissolving the residue in caustic alkali solution and acidifying to precipitate the pure 4-hydroxycoumarin derivative. The product obtained when more than 15 mole per cent of catalyst is used is usually a semi-plastic residue and it is necessary to extract the cooled benzene solution with dilute hydrochloric or sulphuric acid to cause the product to precipitate. In examples, 4-hydroxycoumarin is condensed with benzalacetone by heating in an aqueous medium with (1) and (3) triethylamine; (2) ammonia; (4) aniline, and (5) and (6) tributylamine. U.S.A. Specification 2,427,578 is referred to.
GB5800/52A 1951-07-10 1952-03-05 Manufacture of 4-hydroxycoumarin derivatives Expired GB715846A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US715846XA 1951-07-10 1951-07-10

Publications (1)

Publication Number Publication Date
GB715846A true GB715846A (en) 1954-09-22

Family

ID=22102261

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5800/52A Expired GB715846A (en) 1951-07-10 1952-03-05 Manufacture of 4-hydroxycoumarin derivatives

Country Status (2)

Country Link
FR (1) FR1057063A (en)
GB (1) GB715846A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2487871C1 (en) * 2012-06-25 2013-07-20 Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупроводников и красителей" (ФГУП "ГНЦ "НИОПИК") Method of producing sodium salt 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2h-1-benzopyran-2-one

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2487871C1 (en) * 2012-06-25 2013-07-20 Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупроводников и красителей" (ФГУП "ГНЦ "НИОПИК") Method of producing sodium salt 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2h-1-benzopyran-2-one

Also Published As

Publication number Publication date
FR1057063A (en) 1954-03-04

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