GB640570A - Improvements in or relating to a process for preparing benzodioxane and benzothioxane compounds - Google Patents
Improvements in or relating to a process for preparing benzodioxane and benzothioxane compoundsInfo
- Publication number
- GB640570A GB640570A GB13517/47A GB1351747A GB640570A GB 640570 A GB640570 A GB 640570A GB 13517/47 A GB13517/47 A GB 13517/47A GB 1351747 A GB1351747 A GB 1351747A GB 640570 A GB640570 A GB 640570A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diacetate
- acid
- benzodioxane
- methyl
- hydrogen
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Benzodioxane and benzothioxane derivatives of the formula <FORM:0640570/IV (b)/1> where X is hydrogen, chlorine, methyl, nitro or methoxy, Y is hydrogen or methyl or X and Y together form a benzo group, Z is oxygen or sulphur and R is hydrogen, methyl, vinyl, propenyl, styryl, phenyl, chlorophenyl, dichlorophenyl, nitrophenyl, methylene-dioxyphenyl or furyl, are obtained by heating a compound of the formula <FORM:0640570/IV (b)/2> where M is hydrogen or a salt-forming metal, with an acetate <FORM:0640570/IV (b)/3> where A is chlorine or acetoxy, in the presence of an acid. The reactants are refluxed together at normal or super-atmospheric pressure. In an example, salicylic acid is heated with benzal diacetate and sulphuric acid to give 2-phenyl-4-keto - 1 : 3 - benzodioxane. Other suitable acetates are ethylidene diacetate, 2-chloro-, 2 : 6-dichloro- and 3-nitro-benzal diacetates, piperonal diacetate, furfural diacetate, cinnamal diacetate, crotonal diacetate and allylidene diacetate. Other specified acids are o-cresotinic acid and thiosalicylic acid. The process of Specification 638,556 is disclaimed. A sample has been furnished under Sect. 2 (5) of 2 - phenyl - 4 - keto - 1 : 3 - benzothioxane, prepared from thiosalicylic acid, benzal diacetate and sulphuric acid. The Specification as open to inspection under Sect. 91 contains an example in which sodium salicylate is heated with chloroethyl acetate and potassium iodide in a solvent to give a -acetoxyethyl salicylate. This is separated, purified by fractional distillation under reduced pressure, and heated with sulphuric acid to yield 2 - methyl - 4 - keto - 1 : 3 - benzodioxane. It is stated that other salicylates may be used instead of the sodium salt, and that the acetoxy ester need not be separated from the reaction mixture but merely heated with the addition of acid. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US640570XA | 1946-06-19 | 1946-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB640570A true GB640570A (en) | 1950-07-26 |
Family
ID=22053278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13517/47A Expired GB640570A (en) | 1946-06-19 | 1947-05-20 | Improvements in or relating to a process for preparing benzodioxane and benzothioxane compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB640570A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021073736A1 (en) | 2019-10-16 | 2021-04-22 | Symrise Ag | New aromatic monothioketals as odoriferous substances |
-
1947
- 1947-05-20 GB GB13517/47A patent/GB640570A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021073736A1 (en) | 2019-10-16 | 2021-04-22 | Symrise Ag | New aromatic monothioketals as odoriferous substances |
| CN114746407A (en) * | 2019-10-16 | 2022-07-12 | 西姆莱斯股份公司 | Novel aromatic monothiol ketals as odorants |
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