GB698736A - Manufacture of alkoxy substituted pentanes and tetrahydropyrans - Google Patents

Manufacture of alkoxy substituted pentanes and tetrahydropyrans

Info

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
Application number
GB1126150A
Inventor
Reginald Harold Hall
Brian Keith Howe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB1126150A priority Critical patent/GB698736A/en
Publication of GB698736A publication Critical patent/GB698736A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers 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.
GB1126150A 1950-05-06 1950-05-06 Manufacture of alkoxy substituted pentanes and tetrahydropyrans Expired GB698736A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (4)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
JPS54130587A (en) Carbostyryl derivative
US2421862A (en) Process for producing polyhydric alcohols
GB698736A (en) Manufacture of alkoxy substituted pentanes and tetrahydropyrans
US1945183A (en) Manufacture of alkoxy derivatives of phosphorous acid chlorides
US2312743A (en) Alkoxy meta-dioxanes
US3324187A (en) Production of halogen-substituted, unsaturated alcohols
US2568620A (en) Substituted triazdfes
US2296375A (en) Halogenated meta-dioxanes
EP1516879B1 (en) Process for producing pyran
US2345573A (en) Process for preparing beta-norborneol and its ether
US2517543A (en) Acetals of 2-oxy-tetrahydropyran and tetrahydrofuran-3-aldehydes and process of preparing the same
Barker et al. Reactions of Epoxy Ketones and Alcohols with Amines. Mechanism Studies
US2576901A (en) Preparation of delta-valero-lactones
US3631067A (en) Preparation of coumarin
US2124851A (en) Halogen-substituted alcohols and a process of preparing them
US2262817A (en) Process of preparing unsaturated hydroxy ketones
US2622101A (en) Production of i
US2608557A (en) Method of producing 2-substituted quinolines
US3089896A (en) Preparation of enolates of
GB948136A (en) Preparation of condensed isopropyl silicate materials
GB734142A (en) Process of producing 3-substituted-4-hydroxycoumarins
US2945864A (en) Method of preparing acetal and acetal-like compounds
US2412012A (en) Acetals
US4231970A (en) Reaction products of unsaturated hydrocarbons with P4 S10 and PSX3
US2816930A (en) Aralkyl carbinols