GB805748A - The production of 3-substituted 4-hydroxycoumarins and the 1-thia analogues thereof - Google Patents
The production of 3-substituted 4-hydroxycoumarins and the 1-thia analogues thereofInfo
- Publication number
- GB805748A GB805748A GB1860/57A GB186057A GB805748A GB 805748 A GB805748 A GB 805748A GB 1860/57 A GB1860/57 A GB 1860/57A GB 186057 A GB186057 A GB 186057A GB 805748 A GB805748 A GB 805748A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxy
- hydroxycoumarin
- benzyl
- chlorobenzyl
- 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
- -1 3-substituted 4-hydroxycoumarins Chemical class 0.000 title abstract 4
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical class C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 abstract 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 11
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- WQGHVYDBCGJKAU-UHFFFAOYSA-N C(C1=CC=CC=C1)(C1=CC=CC=C1)C=1C(SC2=CC=CC=C2C1O)=O Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)C=1C(SC2=CC=CC=C2C1O)=O WQGHVYDBCGJKAU-UHFFFAOYSA-N 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 abstract 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- XPSUDKVCLBDZFL-UHFFFAOYSA-N chembl1478716 Chemical compound C1=CC=C2C(O)=CC(=O)SC2=C1 XPSUDKVCLBDZFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 1
- DQDAYGNAKTZFIW-UHFFFAOYSA-N phenprocoumon Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=CC=C1 DQDAYGNAKTZFIW-UHFFFAOYSA-N 0.000 abstract 1
- 239000013049 sediment Substances 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
-
- 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
- C07D311/48—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 with two such benzopyran radicals linked together by a carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Derivatives of 4-hydroxycoumarin and its 1-thia analogue of the general formula <FORM:0805748/IV (b)/1> wherein X is oxygen or sulphur, R is a mono or divalent aromatic hydrocarbon which may be substituted, R1 is a hydrogen atom, an aliphatic hydrocarbon radical or an aromatic hydrocarbon radical which may be substituted, and n is the valency of R, are prepared by (a) reacting n mols. of 4-hydroxy coumarin or its 1-thia analogue of the general formula <FORM:0805748/IV (b)/2> with 1 mol. of a benzyl alcohol of the general formula <FORM:0805748/IV (b)/3> the reaction being carried out at a temperature between 50 DEG and 150 DEG C., in the presence of hydrogen chloride or bromide or an inorganic acid chloride or bromide, or (b) reacting n mols of 4-hydroxycoumarin or its 1-thia analogue of the general formula above with 1 mol. of a chlorine or bromine hydracid ester of a benzyl alcohol as defined above. In an example 2-hydroxy-3-chloro-5-methyl benzyl alcohol and 4-hydroxycoumarin are dissolved or suspended in tetrachlorethane and heated in the presence of hydrogen chloride when 3-(21-hydroxy-31-chloro - 51 - methyl benzyl) - 4 - hydroxy-coumarin is formed and, if desired, converted into its diacetate by boiling with acetic anhydride. Similarly are prepared 3-(a :31-dimethyl - 21 - hydroxy - 51 - chlorobenzyl) -, and 3 - (21 - hydroxy - 31 - methyl - 51 - chlorobenzyl)-4 - hydroxycoumarins, 3 - (21 - hydroxy - 31:51-dichlorobenzyl) - 4 - hydroxycoumarin and its diacetate, 3 - (a - ethyl - benzyl) - 4 - hydroxycoumarin, 2 : 4 - bis - (41 - hydroxycoumarinyl - (31) - methyl) - 6 - methyl phenol and its triacetate, 2 : 6 - bis - (41 - hydroxycoumarinyl - (31)-methyl)-4-tert.-butyl phenol, 3 : 3-bis-(411-hydroxycoumarinyl - (311) - methyl) - 4,41 - dihydroxy - 5,51 - dimethyl diphenyl methane and its tetra-acetate, and 2 : 6-bis-(41-hydroxycoumarinyl - (31) - methyl) - 4 - methyl phenol. Alternatively, benzhydrol in tetrachlorethane is treated with anhydrous hydrogen chloride in the presence of calcium chloride; the liquid separated from the sediment and heated with 4-hydroxy-1-thiacoumarin to form 3-benzhydryl-4 - hydroxy - 1 - thiacoumarin. 3 - (a - Ethyl - benzyl) - 4 - hydroxy - 1 - thiacoumarin, 3 - (a - ethyl - 21 - hydroxy - 31 - methyl - 51 - chlorobenzyl)-, 3 - (a - ethyl - 21 - methoxy - 31 methyl - 41 - chlorobenzyl)-, and 3 - (41 - methoxybenzyl) - 4 - hydroxycoumarins are similarly prepared. 3 - (21 - Methoxy - 31 - methyl - 51 - chlorobenzyl)-, and 3 - (21 - hydroxy - 31:51 - dimethylbenzyl) - 4 - hydroxycoumarins are obtained by heating 4-hydroxycoumarin with an appropriately substituted benzyl alcohol in the presence of phosphorus oxychloride whilst 3-benzhydryl-, 3-benzyl- and 3-(4:41-dichloro - diphenyl) - methyl - 4 - hydroxycoumarins are prepared by heating 4-hydroxycoumarin with benzhydryl chloride, benzyl chloride and 4:41 - dichloro - diphenyl - chloromethane, respectively.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH805748X | 1956-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB805748A true GB805748A (en) | 1958-12-10 |
Family
ID=4538050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1860/57A Expired GB805748A (en) | 1956-01-20 | 1957-01-18 | The production of 3-substituted 4-hydroxycoumarins and the 1-thia analogues thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB805748A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287459A (en) * | 1961-10-23 | 1966-11-22 | Chattanooga Medicine Co | Carbostyrils, coumarines and thiocoumarines |
| DE1263778B (en) * | 1963-06-05 | 1968-03-21 | Spitzner W | Process for the preparation of 3- (alpha-AEthynyl-benzyl) -4-oxycoumarin |
-
1957
- 1957-01-18 GB GB1860/57A patent/GB805748A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287459A (en) * | 1961-10-23 | 1966-11-22 | Chattanooga Medicine Co | Carbostyrils, coumarines and thiocoumarines |
| DE1263778B (en) * | 1963-06-05 | 1968-03-21 | Spitzner W | Process for the preparation of 3- (alpha-AEthynyl-benzyl) -4-oxycoumarin |
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