RARECHEMALBO0588

16.52 g [75 mmol] of 4-tert-butyl-2, 6-dimethylphenylacetic acid and 100 ml of toluene are initially charged in a 250 ml autoclave. After cooling to 0° C., 40 ml of HF are added and the autoclave is closed. The reaction mixture is then stirred at 38-40° C. for 4 hours. Toluene and HF are then distilled off at 20° C/100 mbar. The residue is diluted with 65 ml of water and, with ice-cooling, made alkaline using 100 ml of 10percent strength aqueous sodium hydroxide solution. The solution is extracted once with 65 ml of MTBE and once with 35 ml of MTBE, the aqueous phase is then, with ice-cooling, adjusted to pH 1 using 32percent strength hydrochloric acid, then precipitate formed is dissolved in 130 ml of methylene chloride, the organic phase is dried and the solvent is removed under reduced pressure. This gives 11.91 g of a white solid which, according to GC(sil.), comprises 95.8percent of 2, 6-dimethylphenyl-acetic acid (92.6percent of theory).Intermediate 38: (2, 6-Dimethyl-phenyl)-acetic acid To a mixture of (2, 6-dimethyl-phenyl)-acetic acid ethyl ester (13.3 g, 69.2 mmol) in THF (550 mL) and water (224 mL) was added lithium hydroxide monohydrate (23.2 g, 553 mmol). The resulting mixture was stirred vigorously at rt. After 72 h, the mixture was heated to 50° C. for an additional 24 h. The mixture was cooled to rt and concentrated. To the resulting residue was added aqueous 2 N HCl (300 mL) to afford a colorless precipitate. The precipitate was collected by vacuum filtration and further purified by FCC to provide a colorless solid (8.9 g, 78percent). MS (ESI): mass calcd. for C

Molecular Weight:164.20
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:164.083729621
Monoisotopic Mass:164.083729621
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes