GB804467A - Process for producing a nitro-acetophenone - Google Patents

Process for producing a nitro-acetophenone

Info

Publication number
GB804467A
GB804467A GB25763/55A GB2576355A GB804467A GB 804467 A GB804467 A GB 804467A GB 25763/55 A GB25763/55 A GB 25763/55A GB 2576355 A GB2576355 A GB 2576355A GB 804467 A GB804467 A GB 804467A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydroxide
per cent
phenyl
basic
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
GB25763/55A
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB804467A publication Critical patent/GB804467A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives

Landscapes

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

Abstract

p-Nitroacetophenone is prepared by reacting a -methyl-p-nitrobenzyl nitrate with at least one equivalent of a strongly basic substance (e.g. one of dissociation constant not less than 10-3), if necessary in presence of an inert organic solvent containing up to 25 per cent water. Strongly basic substances are defined as substances which have sufficient basic strength to effect the conversion, and includes both those which are basic as the term is usually understood and those convertible to such bases under the reaction conditions. Reaction temperature may be from 10-110 DEG C., and an inert organic solvent such as an alcohol containing less than 25 per cent water may be employed. Basic substances may be alkali or alkaline earth hydroxides, oxides, alkoxides, hydrides or amides, alkali metal carbonates, amines, quaternary ammonium compounds, or sodium triphenylmethyl. In examples, a -methyl-p-nitrobenzyl nitrate is reacted with (1) piperidine, (2) potassium hydroxide or carbonate, (3) sodium methoxide, (4) benzyl trimethylammonium hydroxide, (5) di-n-butylamine, (6) morpholine, (7) diethanolamine, (8) di-n-propylamine, (9) diethylamine, (10) a quaternary ammonium carbonate polystyrene resin, (11) barium hydroxide, (12) sodium hydroxide, (13) N-phenyl-piperazine, (14) 2,5-dimethyl-piperazine, (15) diethylenetriamine, (16) pyrrolidine. In a further example, the crude nitration product of methyl phenyl carbinol (containing 60 per cent a -methyl-p-nitrobenzyl nitrate) is reacted with potassium hydroxide in methanol. a -Methyl-p-nitrobenzyl nitrate is obtained by reaction of phenyl methyl carbinol with fuming nitric acid at low temperatures.
GB25763/55A 1954-11-01 1955-09-08 Process for producing a nitro-acetophenone Expired GB804467A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US804467XA 1954-11-01 1954-11-01

Publications (1)

Publication Number Publication Date
GB804467A true GB804467A (en) 1958-11-19

Family

ID=22157437

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25763/55A Expired GB804467A (en) 1954-11-01 1955-09-08 Process for producing a nitro-acetophenone

Country Status (1)

Country Link
GB (1) GB804467A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2518894C1 (en) * 2012-10-10 2014-06-10 Федеральное государственное бюджетное учреждение науки Институт высокомолекулярных соединений Российской академии наук Method of obtaining 4-nitroacetophenone
WO2021160468A1 (en) * 2020-02-13 2021-08-19 BASF Agro B.V. Process for the preparation of 1-[4-nitro-2-(trifluoromethyl)phenyl]-alkanones
CN114364655A (en) * 2019-09-12 2022-04-15 巴斯夫农业公司 Preparation method of nitric acid alpha-methyl- [4- (nitro) -2- (trifluoromethyl) ] -benzyl ester

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2518894C1 (en) * 2012-10-10 2014-06-10 Федеральное государственное бюджетное учреждение науки Институт высокомолекулярных соединений Российской академии наук Method of obtaining 4-nitroacetophenone
CN114364655A (en) * 2019-09-12 2022-04-15 巴斯夫农业公司 Preparation method of nitric acid alpha-methyl- [4- (nitro) -2- (trifluoromethyl) ] -benzyl ester
WO2021160468A1 (en) * 2020-02-13 2021-08-19 BASF Agro B.V. Process for the preparation of 1-[4-nitro-2-(trifluoromethyl)phenyl]-alkanones
CN115052853A (en) * 2020-02-13 2022-09-13 巴斯夫农业公司 Preparation method of 1- [ 4-nitro-2- (trifluoromethyl) phenyl ] alkanone

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