GB779849A - Improvements in the production of ethers - Google Patents

Improvements in the production of ethers

Info

Publication number
GB779849A
GB779849A GB21666/55A GB2166655A GB779849A GB 779849 A GB779849 A GB 779849A GB 21666/55 A GB21666/55 A GB 21666/55A GB 2166655 A GB2166655 A GB 2166655A GB 779849 A GB779849 A GB 779849A
Authority
GB
United Kingdom
Prior art keywords
glyoxal
acid
alcohol
dietherified
alcohols
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
GB21666/55A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB779849A publication Critical patent/GB779849A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups

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

Unsymmetrical ethers of derivatives of acid amides containing hydroxy groups with alcohols are manufactured by reacting glyoxal with an amide of a carboxylic acid or of carbonic or thiocarbonic acid in the presence of alcohols, or reacting addition products of one or two mols. of said amides and glyoxal with the above-defined amides in the presence of alcohols, or reacting reaction products of 1, 2 or 3 mols. of one of the said amides and 1 mol. of glyoxal with alcohols. The reactions are preferably carried out in the presence of acid. The products are useful as pharmaceuticals or intermediates. In examples: (1) a :b -bis-carbethoxyaminoethanediol is dietherified by heating with methanol and adding concentrated hydrochloric acid; (2) a :b :b -tricarbethoxyaminoethanol is etherified by heating with benzyl alcohol in the presence of p-toluenesulphonic acid; (3) glyoxol monourein is dietherified by heating with ethyl alcohol and a trace of concentrated hydrochloric acid; (4) the ethyl alcohol in (3) is replaced by methanol; (5) glyoxal is stirred with more than 3 molecular proportions of n-butylurethane in aqueous ethyl alcohol containing hydrochloric acid, to produce the ethyl ether of a :b :b -tricarbo-n-butoxyaminoethanol; (6) glyoxal monothiourein is dietherified as in (3); (7) glyoxal monourein is dietherified by heating with n-octyl alcohol in benzene in the presence of p-toluene-sulphonic acid; (8) the reaction product of 1 mol. of glyoxal and 2 mols. of acetamide is heated with methanol and a trace of concentrated hydrochloric acid to produce a :b -diacetylamino - a :b - dimethoxyethane; (9) the n-octyl alcohol in (7) is replaced by technical dodecyl alcohol; (10) a :b -dicarbethoxyaminoethanediol is heated with urethane, allyl alcohol and a trace of p-toluenesulphonic acid to yield the allyl ether of a :b :b -tricarbethoxyaminoethanol.
GB21666/55A 1954-07-28 1955-07-27 Improvements in the production of ethers Expired GB779849A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE779849X 1954-07-28

Publications (1)

Publication Number Publication Date
GB779849A true GB779849A (en) 1957-07-24

Family

ID=6687296

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21666/55A Expired GB779849A (en) 1954-07-28 1955-07-27 Improvements in the production of ethers

Country Status (1)

Country Link
GB (1) GB779849A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins

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