GB770005A - Process for the manufacture of chromane derivatives - Google Patents
Process for the manufacture of chromane derivativesInfo
- Publication number
- GB770005A GB770005A GB1717654A GB1717654A GB770005A GB 770005 A GB770005 A GB 770005A GB 1717654 A GB1717654 A GB 1717654A GB 1717654 A GB1717654 A GB 1717654A GB 770005 A GB770005 A GB 770005A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethyl
- hydroperoxide
- chroman
- treated
- acid
- 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
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- 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
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,4,4 - trimethyl chroman - 2 - ol, 2,4,4 - trimethyl chromen and bis-2,4,4-trimethyl chroman - 2 - yl peroxide are obtained by a process comprising decomposing 1,1,3-trimethylindane-3-hydroperoxide by reacting the hydroperoxide with an acidic condensation catalyst known to effect the decomposition of hydroperoxides of aromatic compounds to produce phenols and ketones or aldehydes. The decomposition may be carried out under anhydrous conditions, i.e. the reaction medium contains not more than 5 per cent by weight of water, and in this case suitable catalysts are concentrated mineral acids, such as sulphuric and phosphoric acid; organic acids such as p-toluene-sulphonic acid or chlorinated derivatives of acetic acid; Friedel-Crafts catalysts, such as the chlorides of aluminium, tin, iron, zinc and magnesium; acid treated earths such as fuller's earth, bentonite or diatomaceous earth; or silica gel or acid-treated hydrogen ion exchange materials. If the reaction is carried out in an aqueous medium sulphuric acid in concentration from about 5 to 95 per cent by weight is a suitable catalyst. The products of the reaction are 2,2,4 - trimethyl chroman - 2 - ol and 2,4,4-trimethylchroman and some bis - 2,4,4 - trimethyl - chroman 2 - yl peroxide may also be formed as a by-product. A solvent, for example acetone, may be used for the hydroperoxide used in the reaction. In the examples: (a) 1,1,3-trimethylindane - 3 - hydroperoxide is dissolved in acetone and treated with sulphuric acid dissolved in acetone to give a mixture of 2,4,4 - trimethylchroman - 2 - ol and 2,4,6 - trimethyl chroman; (b) trimethylindane hydroperoxide is treated with fuller's earth mixed with benzene to give 2,4,4-trimethyl chromen and the chromanol compound; (c) trimethyl indane hydroperoxide is dissolved in acetone and treated with concentrated sulphuric acid mixed with acetone to give 2,4,4-trimethyl chroman - 2 - ol, 2,4,4 - trimethyl chromen and bis 2,4,4 - trimethylchroman - 2 - yl peroxide of formula <FORM:0770005/IV(b)/1> (d) 2,4,4-trimethyl indane hydroperoxide is treated with commercial mixed alkanesulphonic acid to give 2,4,4 - trimethyl chroman - 2 - ol, 2,4,4 - trimethyl chromen and bis - 2,4,4 - trimethyl chroman-2-yl peroxide; and (c) 2,4,4-trimethyl indane hydroperoxide is treated with sulphuric acid mixed with water to give 2,4,4-trimethyl chromen. Specification 770,006 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1717654A GB770005A (en) | 1954-06-11 | 1954-06-11 | Process for the manufacture of chromane derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1717654A GB770005A (en) | 1954-06-11 | 1954-06-11 | Process for the manufacture of chromane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB770005A true GB770005A (en) | 1957-03-13 |
Family
ID=10090594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1717654A Expired GB770005A (en) | 1954-06-11 | 1954-06-11 | Process for the manufacture of chromane derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB770005A (en) |
-
1954
- 1954-06-11 GB GB1717654A patent/GB770005A/en not_active Expired
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