GB250955A - Manufacture of aromatic aldehydes - Google Patents

Manufacture of aromatic aldehydes

Info

Publication number
GB250955A
GB250955A GB9940/26A GB994026A GB250955A GB 250955 A GB250955 A GB 250955A GB 9940/26 A GB9940/26 A GB 9940/26A GB 994026 A GB994026 A GB 994026A GB 250955 A GB250955 A GB 250955A
Authority
GB
United Kingdom
Prior art keywords
sulphonate
sodium
chlorbenzene
nitro
oxidized
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
GB9940/26A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB250955A publication Critical patent/GB250955A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation

Abstract

250,955. I. G. Farbenindustrie Akt.- Ges., (Assignees of Akt.-Ges. f³r Anilin- Fabrikation). April 15, 1925, [Convention date]. Aromatic aldehydes are made by heating an aralkylamine with a halogen-aryl compound in which the halogen is easily exchanged, e.g. dinitrochlorbenzene, 2 - nitro-1-chlorbenzene-4-sulphonic acid or 4-nitro-1-chlorbenzene-2-sulphonic acid, and oxidizing the product in acid solution. In examples (1) the hydrochloride of 2 : 4-dimethylbenzylamine is heated with sodium 4- nitro-1-chlorbenzene-2-sulphonate and sodium carbonate, the sodium 2: 4-dimethyl-1-benzylamino-4-nitrobenzene-2-sulphonate formed is dissolved in water and treated with sodium bichromate and sulphuric acid, the resulting 2 : 4-dimethylbenzaldehyde being distilled over with steam, (2) 4-methoxybenzylamine is similarly treated with sodium 2-nitro-1-chlorbenzene-4-sulphonate, the intermediate product, sodium 4'- methoxy - 1-benzylamino-2-nitrobenzena-4-sulphonate, being finally oxidized to anisaldehyde, (3) vanillylamine hydrochloride and potassium 2:6 dinitro-1-chlorbenzene-4-sulphonate yield potassium 4<1>-oxy-3<1>-methoxy-1-benzylamino-2 : 6-dinitrobenzene-4-sulphonate, which is oxidized to vanillin, (4) 4-methyl-3-chlorbenzylamine hydrochloride (obtained from o-chlortoluene and chlormethylphthalimide by the process described in Specification 249,883), and sodium 4-nitro-1-chlorbenzene-2-sulphonate yield sodium 4'-methyl-3'- chlor - 1-benzylamino-4-nitrobenzene-2-sulphonate, which is oxidized to 4-methyl-3-chlorbenzaldehyde, (5) phenylethylamine hydrochloride and sodium 4-nitro-1-chlorbenzene-2-sulphonate yield sodium 1-phenylethylamino-4-nitrobenzene-2-sulphonate, which is oxidized to phenylacetaldehyde, and (6) 1-naphthylmethylamine and sodium 4- nitro-1-chlorbenzene-2-sulphonate yield sodium 1 - naphthylmethylamino-4-nitrobenzene-2-sulphonate, which is oxidized to 1-naphthaldehyde.
GB9940/26A 1925-04-15 1926-04-15 Manufacture of aromatic aldehydes Expired GB250955A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE250955X 1925-04-15

Publications (1)

Publication Number Publication Date
GB250955A true GB250955A (en) 1927-05-26

Family

ID=5940522

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9940/26A Expired GB250955A (en) 1925-04-15 1926-04-15 Manufacture of aromatic aldehydes

Country Status (2)

Country Link
FR (1) FR614146A (en)
GB (1) GB250955A (en)

Also Published As

Publication number Publication date
FR614146A (en) 1926-12-07

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