O-Nitrobenzoyl chloride

CAUTION. The preparation of o-nitrobenzoyl chloride, o-nitrophenacetyl chloride and all o nitroacid chlorides should not be attempted by the above methods a violent explosion may occur upon distilling the product or when the last traces of thionyl chloride are removed in vacuo at 100°. Perhaps the safest method is to treat the pure acid in benzene solution with 1 1 mols of thionyl chloride and to reflux until evolution of sulphur dioxide and hydrogen chloride has ceased the solution of the acid chloride in benzene may then bo employed for most reactions. 

Step A Preparation of (2 -isopropylidenedioxy)-propyl o-nitrobenzoate-SSS g of 2 -di-methyl4-hydroxymethyl-1 -dloxolane were dissolved under agitation In 60 cc of anhydrous pyridine. The solution was cooled to i-5 G and 86.5 g of o-nitrobenzoyl chloride (prepared by Leckermann et a., 8er. vol. 80,p.488,1947) were slowly introduced Into it. The reaction mixture was agitated for a period of two hours at room temperature and then was poured into 500 cc of ether. The mixture was filtered and the filtrate was washed successively with 0.5 N sulfuric acid solution, with aqueous sodium bicarbonate solution and finally with water until the wash waters were neutral. The washed solution was dried over sodium sulfate and filtered again. The filtrate was distilled to dryness under vacuum to obtain 116.5 g (being a yield of 92%) of (2,3-isopropylidenedioxy)-propyl o-nitrobenzoate in the form of a yellow oil which distilled at 178 to 180°C at a pressure of 1 mm. 

Handling. The refs discuss the expl properties of o-nitrobenzoyl chloride and o-nitrophenacetyl chloride, both of which are Likely to expld when heated to over 100°. It is suggested that these compds be prepd and utilized in soln without... 

Malonic ester synthesis, 7 acylation by o-nitrobenzoyl chloride, 70... 

The o-nitrobenzoyl chloride can be prepared from the commercially available acid and thionyl chloride. 

H (1947) (Hazards from chlorates perchlorates in admixtures) 43)May Baker Ltd, Chem Ind 1946, 89 CA 40, 2985 (1946) (Hazards in handling o-Nitro aromatic compds) 44)W. A.Bonner C.D.Hurd, JACS 68, 344-45 (1946) (Hazard involved in distillation of o-Nitrobenzoyl chloride) 45)W.G.Bailey A.Roy, JSCI 65, 421-22 (1946)... 

CAUTION The preparation of o-nitrobenzoyl chloride, o-nitrophenacetyl chloride and all o-nitroacid chlorides should not be attempted by the above methods a violent explosion may occur upon distilling the product. 

Malonic ester, ethoxymagnesium derivative, solution of, 30, 70 Malonic ester synthesis, 30, 7 acylation by o-nitrobenzoyl chloride, 30, 70... 

Nitrobenzophenone, 32, 12 o-Nitrobenzoyl chloride, 30, 70 o-Nitrochlorobenzene, 32, 24 9-Nitro-10-chloro-9,10-dihydroanthra-... 

In another synthesis the product of acylation of ethoxymagnesiummalonic ester with o-nitrobenzoyl chloride is converted by acid hydrolysis-decarboxylation into poa... 

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