Laboratory Synthesis Of Benorilate/Benorylate/Benorilato

synthesis of Benorilate

IUPAC NAME Benorilate CN: 2- (acetyl oxy )benzoic acid 4- (acetyl amino )phenyl ester

Use: analgesic, antirheumatic.it is a pro drug of paracetamol

Benorilate MW: 313.31 

Benorilate MF: C17H15NO5
Benorilate LD50: 1551 mg/kg (M, p.o.);3500 mg/kg (R, p.o.)

Partition Coefficient.

Log P(octanol/water), 2.2.

Colour Tests.

Liebermann's test—black; Mandelin's test—green; Marquis test—violet.

Thin–layer Chromatography.

System TA—Rf 67; system TB—Rf 00; system TC—Rf 51; system TL—Rf 62; system TAE—Rf 86. (Marquis reagent, positive.)

Gas Chromatography.

System GA—benorilate RI 1840, aspirin RI 1309, paracetamol RI 1687.

High Performance Liquid Chromatography.

System HD—benorilate k 0.7, aspirin k 0.5, paracetamol k 0.1; system HW—benorilate k 22.4, aspirin k 2.7, paracetamol k 0.32.

Ultraviolet Spectrum.

Dehydrated alcohol—240 nm (A¹₁=740a).

Reference(s):
Clarke's Analysis of Drugs and Poisons
US 3 431 293 (Sterling Drug; 4.3.1969; GB-prior. 9.4.1964).
FR 1 436 870 (Sterwin; appl. 8.4.1965; GB-prior. 9.4.1964).