Butyl formate

Into a 250 or 500 ml. round-bottomed flask provided with a reflux condenser place 46 g. (38 ml.) of A.R. formic acid (98/100 per cent.) and 37 g. (46 ml.) of n-butyl alcohol. Reflux for 24 hours. Wash the cold mixture with small volumes of saturated sodium chloride solution, then with saturated sodium bicarbonate solution in the presence of a httle 

Place 146 g. of adipic acid, 360 ml, (285 g.) of absolute ethyl alcohol 180 ml. of toluene and 1 - 5 g. of concentrated sulphuric acid in a 1-litre round-bottomed flask, attach a short fractionating column connected to a downward condenser, and heat in an oil bath at 115°, When the acid 

Place 100 g. of adipic acid in a 750 ml. round-bottomed flask and add successively 100 g. (127 ml.) of absolute ethyl alcohol, 250 ml. of sodium-dried benzene and 40 g. (22 ml.) of concentrated sulphuric acid (the last-named cautiously and with gentle swirling of the contents of the flask). Attach a reflux condenser and reflux the mixture gently for 5-6 hours. Pour the reaction mixture into excess of water (2-3 volumes), separate the benzene layer (1), wash it with saturated sodium bicarbonate solution until eflfervescence ceases, then with water, and dry with anhydrous magnesium or calcium sulphate. Remove most of the benzene by distillation under normal pressure until the temperature rises to 100° using the apparatus of Fig. II, 13, 4 but substituting a 250 ml. Claisen flask for the distilling flask then distil under reduced pressure and collect the ethyl adipate at 134-135°/17 mm. The yield is 130 g. 

Diethyl oxalate. Reflux a mixture of 45 g. of anhydrous oxalic acid (1), 81 g. (102-5 ml.) of absolute ethyl alcohol, 190 ml. of sodium-dried benzene and 30 g. (16-5 ml.) of concentrated sulphuric acid for 24 hours. Work up as for Diethyl Adipate and extract the aqueous laj er with ether distil under atmospheric pressure. The yield of ethyl oxalate, b.p. 182-183°, is 57 g. 

Place 100 g. of adipic acid in a 750 ml. round-bottomed flask and add successively 100 g. (127 ml.) of absolute ethyl alcohol, 250 ml. of sodium-dried benzene and 40 g. (22 ml.) of concentrated sulphuric acid (the last-named cautiously and with gentle swirling of the contents of the flask). Attach a reflux condenser and reflux the mixtiu e gently for 

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Methyl formate. Ethyl formate Methyl acetate Iso-propyl formate Ethyl acetate Methyl propionate "-Propyl formate Iso-propyl acetate Methyl iso-butyrate Iso-butyl formate. Ethyl propionate M-Propyl acetate. Methyl butyrate. ... 

M-Butyl formate. Ethyl iso-butyrate IsO -butyl acetate Ethyl butyrate -Propyl propionate Iso-amyl formate, -But> l acetate Iso-propyl butyrate Iso-butyl propionate n-Propyl -butyrate -Butyl propionate Iso-butyl isobutyrate Ethyl lactate Iso-butyl butyrate Cycloheicyl formate -Butyl -butyrate Iso-propyl lactate. Cyclohexyl acetate Diethyl oxalate Di-iao-propyl oxalate... 

Formic acid n-Butyl alcohol n-Butyl formate... 

Formate Esters Methyl formate Ethyl formate Propyl formate Isopropyl formate Butyl formate Isobutyl formate... 

Exposure of compound 16, a substance that can be obtained in a straightforward manner from glycine, to sodium tert-butoxide furnishes an enolate that undergoes conversion to 8 upon treatment with terf-butyl formate. It was anticipated that the phthalimido and tert-butyl ester protecting groups in 8 could be removed easily and selectively under anhydrous conditions at a later stage in the synthesis. 

Butyl ether, see Dibutyl ether n-Butyl formate 0.91 3.5 18 322... 

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