GB698736A - Manufacture of alkoxy substituted pentanes and tetrahydropyrans - Google Patents
Manufacture of alkoxy substituted pentanes and tetrahydropyransInfo
- Publication number
- GB698736A GB698736A GB1126150A GB1126150A GB698736A GB 698736 A GB698736 A GB 698736A GB 1126150 A GB1126150 A GB 1126150A GB 1126150 A GB1126150 A GB 1126150A GB 698736 A GB698736 A GB 698736A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkoxy
- tetrahydropyran
- butoxy
- methyl
- dihydropyran
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises 2 : 6-diethoxy- and 2 : 6 - n - butoxy - tetrahydropyran, 1 : 1 : 5 : 5 - tetra-n-butoxypentane and a process for preparing compounds of the general formul <FORM:0698736/IV (b)/1> and <FORM:0698736/IV (b)/2> wherein R1 represents a hydrogen atom or an alkyl, aryl or alkoxy alkyl group, R2 and R3 represent hydrogen atoms or alkyl or aryl groups and R represents a primary or secondary alkyl group of 1 to 6 carbon atoms, by reacting a compound of the general formula <FORM:0698736/IV (b)/3> wherein R, R1, R2 and R3 have the above significance, with the required primary or secondary alcohol under substantially anhydrous conditions in the presence of an acid condensation catalyst. If the amount of alcohol used is about one mole. to one mole. of the dihydropyran starting material, the tetrahydropyran product is mainly formed, further quantities of alcohol lead to the formation of the substituted pentanes. Suitable acid condensation catalysts are hydrochloric, phosphoric and sulphuric acid. The reaction may be carried at a temperature in the range between 0 and 100 DEG C., and preferably at a temperature below 60 DEG C. Starting materials which may be used in the process are 6 - alkoxy -, 6 - alkoxy - 3 - methyl -, 6 - alkoxy - 4 - methyl -, 6 - alkoxy - 5 - methyl - and 6 - alkoxy - 4 - phenyl - delta2 - dihydropyran. In the examples the following compounds are prepared: 2,6-diethoxy- and 2,6-di-n - butoxy - tetrahydropyran and 1,1,5,5 - tetraethoxy - and 1,1,5,5 - tetra - n - butoxy - tetrahydropyran are prepared and are each converted to glutardialdehyde bis-2 : 4-dinitrophenylhydrazone. Other compounds mentioned are 2,6 - dimethoxy -, 2,6 - diethoxy - 5 - methoxymethyl - and 2,6 - di - n - butoxy - 3,4 - dimethyl - tetrahydropyran, and 1,1,5,5, - tetramethoxy -, 1,1,5,5, - tetraethoxy - 2 - methoxymethyl -, and 1,1,5,5 - tetra - n - butoxy - 2,3 - dimethyl - pentane. 6 - Alkoxy -, 6 - alkoxy - methyl -, 6 - alkoxy - 4 - methyl - and 6 - alkoxy - 4 - phenyl - delta2 - dihydropyran are obtained by the interaction of acrolein, alpha-methacrolein, crotonaldehyde or cinnomaldehyde respectively with an alkyl vinyl ether. In an example, 6-ethoxy-delta2-dihydropyran is obtained by heating acrolein and ethyl vinyl ether in the presence of hydroquinone.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1126150A GB698736A (en) | 1950-05-06 | 1950-05-06 | Manufacture of alkoxy substituted pentanes and tetrahydropyrans |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1126150A GB698736A (en) | 1950-05-06 | 1950-05-06 | Manufacture of alkoxy substituted pentanes and tetrahydropyrans |
Publications (1)
Publication Number | Publication Date |
---|---|
GB698736A true GB698736A (en) | 1953-10-21 |
Family
ID=9982972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1126150A Expired GB698736A (en) | 1950-05-06 | 1950-05-06 | Manufacture of alkoxy substituted pentanes and tetrahydropyrans |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB698736A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2885443A (en) * | 1956-04-09 | 1959-05-05 | Quaker Chemical Products Corp | Water-soluble acetals of glutaralde-hyde and method of making same |
US2931837A (en) * | 1956-04-13 | 1960-04-05 | Union Carbide Corp | Long chain alkoxy-diols |
US3023243A (en) * | 1956-10-19 | 1962-02-27 | Union Carbide Corp | Long chain alkoxy diamines |
US3232907A (en) * | 1962-04-09 | 1966-02-01 | Du Pont | Dicyclic acetal polymers and process for their preparation |
-
1950
- 1950-05-06 GB GB1126150A patent/GB698736A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2885443A (en) * | 1956-04-09 | 1959-05-05 | Quaker Chemical Products Corp | Water-soluble acetals of glutaralde-hyde and method of making same |
US2931837A (en) * | 1956-04-13 | 1960-04-05 | Union Carbide Corp | Long chain alkoxy-diols |
US3023243A (en) * | 1956-10-19 | 1962-02-27 | Union Carbide Corp | Long chain alkoxy diamines |
US3232907A (en) * | 1962-04-09 | 1966-02-01 | Du Pont | Dicyclic acetal polymers and process for their preparation |
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