DE951927C - Process for the preparation of meta- (chloromethyl) benzoic acid - Google Patents

Process for the preparation of meta- (chloromethyl) benzoic acid

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Publication number
DE951927C
DE951927C DEB7120D DEB0007120D DE951927C DE 951927 C DE951927 C DE 951927C DE B7120 D DEB7120 D DE B7120D DE B0007120 D DEB0007120 D DE B0007120D DE 951927 C DE951927 C DE 951927C
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DE
Germany
Prior art keywords
benzoic acid
chloromethyl
meta
preparation
parts
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
DEB7120D
Other languages
German (de)
Inventor
Dr Werner Rohland
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
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 filed Critical BASF SE
Priority to DEB7120D priority Critical patent/DE951927C/en
Application granted granted Critical
Publication of DE951927C publication Critical patent/DE951927C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von meta-(Chlormethyl)-benzoesäure Es wurde gefunden, daß man in einfacher Weise meta-(Chlormethyl)-benzosäure in guten Ausbeuten erhält, wenn man Benzoesäure in Oleum enthaltender Schwefelsäure mit Dichlordimethyläther umsetzt.Process for the preparation of meta- (chloromethyl) benzoic acid It has been found that meta- (chloromethyl) benzoic acid can be obtained in good yields in a simple manner obtained when benzoic acid in oleum containing sulfuric acid with dichlorodimethyl ether implements.

Die so erhaltene meta-(Chlormethyl) -benzoesäure ist ohne weiteres sehr rein. Sie kann durch Umlösen oder Destillieren völlig rein gewonnen werden und ist ein wertvolles Zwischenprodukt, insbesondere zur Herstellung von Farbstoffen und Kunststoffen. The meta- (chloromethyl) benzoic acid thus obtained is readily available very pure. It can be obtained completely pure by dissolving or distilling and is a valuable intermediate product, especially for the manufacture of dyes and plastics.

Es ist bekannt, die Chlormethylierung aromatischer Oxycarbonsäuren durch Umsetzung mit Formaldehyd oder Formaldehyd abspaltenden Verbindungen in Gegenwart konzentrierter Halogenwasserstoffsäuren auszuführen. Man hat ferner die Chlormethylierung aromatischer Oxyaldehyde durch Umsetzung mit Formaldehyd oder Formaldehyd abspaltenden Verbindungen bereits in Gegenwart konzentrierter Schwefelsäure vorgenommen. Versucht man indessen, Benzoesäure unter Verwendung von konzentrierter Schwefelsäure mit Dichlordimethyläther umzusetzen, so erhält man aus dem Umsetzungsgemisch an Stelle der erwarteten meta-(Chlormethyl)-benzoesäure lediglich unveränderte Benzoesäure. Daher war es überraschend und bedeutet ein Bereicherung der Technik, daß Benzoesäure sich bei Anwendung von Oleum enthaltender Schwefelsäure und Dichlordimethyläther in guter Ausbeute zu reiner, einheitlicher meta-(Chlormethyl)-bensoesäure umsetzen läßt. The chloromethylation of aromatic oxycarboxylic acids is known by reaction with formaldehyde or formaldehyde-releasing compounds in the presence concentrated hydrohalic acids. There is also chloromethylation aromatic oxyaldehyde by reaction with formaldehyde or splitting off formaldehyde Compounds already made in the presence of concentrated sulfuric acid. Tries one meanwhile, benzoic acid using concentrated sulfuric acid with To implement dichlorodimethyl ether, one obtains from the reaction mixture in place the expected meta- (chloromethyl) -benzoic acid only unchanged benzoic acid. It was therefore surprising and an asset to the art that benzoic acid when using sulfuric acid and dichlorodimethyl ether containing oleum convert in good yield to pure, uniform meta- (chloromethyl) benzoic acid leaves.

Die im folgenden Beispiel genannten Teile sind Gewichtsteile. The parts mentioned in the following example are parts by weight.

Beispiel 250 Teile Benzoesäure und 5ooTeileDichlordimethyläther werden in einem Gemisch aus 540 Teilen Schwefelsäuremonohydrat und IOO Teilen 240/,dem Oleum gelöst. Das Ganze wird dann unter Rühren 6 Stunden auf 50° erwärmt. Nach dem Erkalten gießt man das Umsetzungsgemisch in Eiswasser und behandelt die ausgeschiedene Masse mehrmals mit kaltem Wasser. Der Rückstand wird in Benzol gelöst, die Benzollösung getrocknet und dann destilliert. Man erhält so etwa 200 Teile meta-(Chlormethyl)-benzoesäure. Example 250 parts of benzoic acid and 500 parts of dichlorodimethyl ether are used in a mixture of 540 parts of sulfuric acid monohydrate and 100 parts of 240 /, the Dissolved oleum. The whole is then heated to 50 ° for 6 hours while stirring. After this To cool, the reaction mixture is poured into ice water and the precipitated is treated Mass several times with cold water. The residue is dissolved in benzene, the benzene solution dried and then distilled. About 200 parts of meta- (chloromethyl) benzoic acid are obtained in this way.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von meta-(Chlormethyl)-benzoesäure, dadurch gekennzeichnet, daß man Benzoesäure in Oleum enthaltender Schwefelsäure mit Dichlordimethyläther umsetzt. PATENT CLAIM Process for the production of meta- (chloromethyl) -benzoic acid, characterized in that benzoic acid is used in sulfuric acid containing oleum reacted with dichlorodimethyl ether. In Betracht gezogene Druckschriften: Deutsche Patentschtiften Nr. II3 723, II4 I94; Chemisches Zentralblatt, I939, II., S. 4466, I920, III., S. 449 bis 451. Publications considered: German Patent Papers No. II3 723, II4 I94; Chemisches Zentralblatt, I939, II., P. 4466, I920, III., P. 449 to 451.
DEB7120D 1943-08-21 1943-08-21 Process for the preparation of meta- (chloromethyl) benzoic acid Expired DE951927C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB7120D DE951927C (en) 1943-08-21 1943-08-21 Process for the preparation of meta- (chloromethyl) benzoic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB7120D DE951927C (en) 1943-08-21 1943-08-21 Process for the preparation of meta- (chloromethyl) benzoic acid

Publications (1)

Publication Number Publication Date
DE951927C true DE951927C (en) 1956-11-08

Family

ID=6955134

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB7120D Expired DE951927C (en) 1943-08-21 1943-08-21 Process for the preparation of meta- (chloromethyl) benzoic acid

Country Status (1)

Country Link
DE (1) DE951927C (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE114194C (en) *
DE113723C (en) * 1899-01-14

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE114194C (en) *
DE113723C (en) * 1899-01-14

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