GB438361A - Improvements in or relating to the manufacture of coumarin - Google Patents
Improvements in or relating to the manufacture of coumarinInfo
- Publication number
- GB438361A GB438361A GB14348/34A GB1434834A GB438361A GB 438361 A GB438361 A GB 438361A GB 14348/34 A GB14348/34 A GB 14348/34A GB 1434834 A GB1434834 A GB 1434834A GB 438361 A GB438361 A GB 438361A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- acetic anhydride
- cobalt
- anhydride
- coumarin
- 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
Links
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title abstract 8
- 229960000956 coumarin Drugs 0.000 title abstract 4
- 235000001671 coumarin Nutrition 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 18
- 150000003839 salts Chemical class 0.000 abstract 4
- OPPZJAAVEDSDPQ-UHFFFAOYSA-N 3-acetyl-2-hydroxybenzaldehyde Chemical compound CC(=O)C1=CC=CC(C=O)=C1O OPPZJAAVEDSDPQ-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 229910017052 cobalt Inorganic materials 0.000 abstract 3
- 239000010941 cobalt Substances 0.000 abstract 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 3
- XLOFQRZBFLSDLY-UHFFFAOYSA-N (1,6-dichloro-6-methylcyclohexa-2,4-dien-1-yl) hydrogen carbonate Chemical compound C(O)(=O)OC1(C=CC=CC1(C)Cl)Cl XLOFQRZBFLSDLY-UHFFFAOYSA-N 0.000 abstract 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000012346 acetyl chloride Substances 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 229910000428 cobalt oxide Inorganic materials 0.000 abstract 2
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 abstract 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052797 bismuth Inorganic materials 0.000 abstract 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/10—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring unsubstituted
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Coumarin is prepared by heating salicylic aldehyde or an acetylsalicylic aldehyde with acetic anhydride in the presence of an oxide or salt of cobalt. Alternatively, o -dichloro-o-cresol carbonate is heated with acetic anhydride in the presence of an oxide or salt of cobalt, whereby an acetylsalicylic aldehyde is first produced (with evolution of acetyl chloride), and is then converted into coumarin by the further action of the anhydride. The reaction may be effected at atmospheric or other pressure. In the examples: (1) o -dichlor-o-cresol carbonate and an excess of acetic anhydride are heated with a small proportion of cobalt oxide; acetyl chloride is first evolved, followed by the excess of acetic anhydride and the acetic acid formed; coumarin is recovered from the residue; (2) acetylsalicylic aldehyde and acetic anhydride are heated with a small proportion of cobalt oxide. The Specification as open to inspection under Sect. 91 states that an oxide or a carbonate, chloride or other salt of bismuth or zinc may be used in place of an oxide or salt of cobalt. It states also that acetic anhydride may be replaced by another anhydride, such as butyric, benzoic or phthalic anhydride. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH438361X | 1933-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB438361A true GB438361A (en) | 1935-11-11 |
Family
ID=4515121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14348/34A Expired GB438361A (en) | 1933-05-12 | 1934-05-11 | Improvements in or relating to the manufacture of coumarin |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB438361A (en) |
-
1934
- 1934-05-11 GB GB14348/34A patent/GB438361A/en not_active Expired
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