GB720584A - 5-benzyloxy-ª‰,2-dinitrostyrenes and a process for their preparation - Google Patents

5-benzyloxy-ª‰,2-dinitrostyrenes and a process for their preparation

Info

Publication number
GB720584A
GB720584A GB3760/53A GB376053A GB720584A GB 720584 A GB720584 A GB 720584A GB 3760/53 A GB3760/53 A GB 3760/53A GB 376053 A GB376053 A GB 376053A GB 720584 A GB720584 A GB 720584A
Authority
GB
United Kingdom
Prior art keywords
benzyloxy
nitro
prepared
alcohol
nitromethylbenzyl
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
GB3760/53A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB720584A publication Critical patent/GB720584A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/12Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/08Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 5-benzyloxy-b ,2-dinitrostyrenes having the general formula <FORM:0720584/IV (b)/1> in which X is phenyl, halophenyl, lower alkylphenyl or lower alkoxyphenyl, Y is hydrogen, phenyl, halophenyl, lower alkylphenyl or lower alkoxyphenyl and R is hydrogen or lower alkyl. The compounds are prepared by treating a 5-benzyloxy - 2 - nitro - a - (1 - nitroalkyl - 1) benzyl alcohol of the formula <FORM:0720584/IV (b)/2> with a dehydrating agent, e.g. acetic anhydride with or without an alkali metal salt; potassium acid sulphate, oxalic acid, phthalic anhydride and phosphorus pentoxide and pyridine. The starting material may be prepared by the condensation of a 5-benzyloxy-2-nitrobenzaldehyde with a 1-nitroalkane in the presence of an alkali metal hydroxide. In examples (1) and (2) 5 - benzyloxy - 2 - nitro - a - nitromethylbenzyl alcohol (prepared by condensing 5-benzyloxy-2-nitrobenzaldehyde with nitromethane in the presence of potassium hydroxide and aqueous alcohol) is heated with anhydrous sodium acetate and acetic anhydride to yield 5-benzyloxy - b ,2 - dinitrostyrene; (3) 5 - benzyloxy - b ,2 - dinitro - b - methylstyrene is prepared similarly from 5 - benzyloxy - 2 - nitro - a - (1 - nitroethyl - 1) benzyl alcohol using acetic anhydride as dehydrating agent; (4) 5-benzyloxy - b ,2 - dinitro - b - ethylstyrene is prepared from 5 - benzyloxy - 2 - nitro - 2 - (1 - nitro - propyl - 1) benzyl alcohol using oxalic acid as dehydrating agent; (5) 5-(p,p1-dimethoxybenzhydryloxy) - b , 2 - dinitrostyrene is prepared by dehydrating 5 - (p,p1 - dimethoxybenzydryloxy) - 2 - nitro - a - nitromethylbenzyl alcohol; (6) 5 - benzhydryloxy - b ,2 - dinitrostyrene is prepared by dehydrating 5-benzhydryloxy-2-nitro - a - nitromethylbenzyl alcohol; (7) 5 - (p,p1 - dimethylbenzhydryloxy) - b ,2 - dinitrostyrene is prepared from 5 -(p,p - dimethylbenzhydryloxy) - 2 - nitro - a - nitromethylbenzyl alcohol; and (8) 5 - (p,p1 - dichlorobenzhydryloxy) - b ,2 - dinitrostyrene is prepared by dehydrating 5 - (p,p1 - dichlorobenzhydryloxy) 2 - nitro - a - nitromethylbenzyl alcohol with phthalic anhydride. Many other substituted 5-benzyloxy-b ,2-dinitrostyrenes of the above general formula are specified. p
GB3760/53A 1952-02-23 1953-02-10 5-benzyloxy-ª‰,2-dinitrostyrenes and a process for their preparation Expired GB720584A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US720584XA 1952-02-23 1952-02-23

Publications (1)

Publication Number Publication Date
GB720584A true GB720584A (en) 1954-12-22

Family

ID=22105296

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3760/53A Expired GB720584A (en) 1952-02-23 1953-02-10 5-benzyloxy-ª‰,2-dinitrostyrenes and a process for their preparation

Country Status (1)

Country Link
GB (1) GB720584A (en)

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