GB605999A - Process for the production of coumarins - Google Patents

Process for the production of coumarins

Info

Publication number
GB605999A
GB605999A GB385146A GB385146A GB605999A GB 605999 A GB605999 A GB 605999A GB 385146 A GB385146 A GB 385146A GB 385146 A GB385146 A GB 385146A GB 605999 A GB605999 A GB 605999A
Authority
GB
United Kingdom
Prior art keywords
give
carbonate
hydroxycoumarin
sodium
hydroxyacetophenone
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
GB385146A
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.)
Ward Blenkinsop and Co Ltd
Original Assignee
Ward Blenkinsop and 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
Priority to BE470996D priority Critical patent/BE470996A/xx
Application filed by Ward Blenkinsop and Co Ltd filed Critical Ward Blenkinsop and Co Ltd
Priority to GB385146A priority patent/GB605999A/en
Priority to FR941418D priority patent/FR941418A/en
Publication of GB605999A publication Critical patent/GB605999A/en
Priority to DEP29759A priority patent/DE806458C/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)
  • Pyrane Compounds (AREA)

Abstract

4-Hydroxycoumarins are prepared by condensing a dialkyl or diaralkyl carbonate with an o-hydroxyacylophenone of the formula <FORM:0605999/IV(b)/1> in which R is an alkyl group, in the presence of an alkali metal alcoholate, whether added as such or formed in situ, and treating the resulting product with acid. An excess of the carbonate may be employed, and a solvent (e.g. benzene, toluene, or xylene) forming a low-boiling azeotrope with the alcohol liberated may be used. The ketone reactant may be o-hydroxybutyrophenone, or may have substituents such as alkyl groups in the benzene ring. The products may be condensed with aldehydes to give dihydroxy dicoumarins, e.g. with formaldehyde to give 3.31-methylene-bis-(4-hydroxycoumarin). In examples: (1) sodium ethoxide, diethyl carbonate and o-hydroxyacetophenone or o-hydroxypropiophenone are reacted together to give 4-hydroxycoumarin; (2) dibenzyl carbonate is reacted with o-hydroxyacetophenone and with either sodium or sodium and alcohol to give 4-hydroxycoumarin.
GB385146A 1946-02-07 1946-02-07 Process for the production of coumarins Expired GB605999A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE470996D BE470996A (en) 1946-02-07
GB385146A GB605999A (en) 1946-02-07 1946-02-07 Process for the production of coumarins
FR941418D FR941418A (en) 1946-02-07 1947-02-06 Process for preparing cyclic lactones
DEP29759A DE806458C (en) 1946-02-07 1949-01-01 Process for the production of coumarins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB385146A GB605999A (en) 1946-02-07 1946-02-07 Process for the production of coumarins

Publications (1)

Publication Number Publication Date
GB605999A true GB605999A (en) 1948-08-04

Family

ID=9766120

Family Applications (1)

Application Number Title Priority Date Filing Date
GB385146A Expired GB605999A (en) 1946-02-07 1946-02-07 Process for the production of coumarins

Country Status (4)

Country Link
BE (1) BE470996A (en)
DE (1) DE806458C (en)
FR (1) FR941418A (en)
GB (1) GB605999A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960813C (en) * 1951-06-20 1957-03-28 Distillers Co Yeast Ltd Process for the production of unsaturated ª † and ª € lactones

Also Published As

Publication number Publication date
BE470996A (en)
FR941418A (en) 1949-01-11
DE806458C (en) 1951-06-14

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