Methyl p-tert-butylphenylacetate

Methyl p-tert-butylphenylacetate is an endogenous metabolite.

Colourless oily liquid; sweet, somewhat woody-camphoraceous odour

Preparation 11 Methyl 2-(4-t-butylphenyl)propanoate 23.3 mL of lithium bis(trimethylsilyl)amide (1.0 M, 23 mmols) was added dropwise to 4.75 g (23 mmols) of Methyl 4-tert-butylphenylacetate (4.13g, 20 mmol) was dissolved in MeOH (160 mL) and treated with water (40 mL) and NaOH(1.2 g, 30 mmol). The reaction was stirred at room temperature overnight. Thevolatiles were removed under reduced pressure and the remaining residue wasdiluted with water and acidified to pH 4 with 1 N sulfuric acid. The resultingsolids were filtered, washed with water and dried to give 4-tert-butylphenylacetic acid 8a as a white solid (39percent). 1H NMR (400 MHz, CDCl3) deltaH 1.32 (s, 9 H), 3.60 (s, 2 H), 7.22 (d, J = 8.2 Hz, 2 H), 7.35(d, J = 8.2 Hz, 2 H), 8.48 (s, 1 H)ppm; 13C NMR (101 MHz, CDCl3) deltaC 31.49 (3), 34.62, 40.84, 125.70 (2), 129.16 (2), 130.57, 150.29, 177.92 ppm.To a round bottom flask equipped with a stir bar was added methyl 4-t-butylphenylacetate (5.185 g, 25.13 mmol), 125 mL THF, 25 mL water and LiOH H20 (1.054 g, 25.12 mmol). The reaction was stirred overnight then evaporated in vacuo to give an aqueous residue which was diluted with 25 mL water. The solution was then filtered over a nylon disk and the filtrate acidified with 50 mL 1 N HCI. The precipitated solid that formed was collected by filtration, rinsed with water and dried to yield the product, 4-T- butylphenylacetic acid, as a white powder (4.572 g, 23.8 mmol). 1H NMR (DMSO-d6) : 8 12.28 (br s, 1H), 7.33 (d, 2H), 7.18 (d, 2H), 3.51 (s, 2H), 1.28 (s, 9H); MS: m/z 191.0 (M-H)-.(1) To a solution of 4-tert-butylphenyl acetic acid methyl ester (10.0 g, 48.5 mmol) in a mixture of tetrahydrofuran (50 mL) and methanol (50 mL) was added 6 mol/L aqueous sodium hydroxide solution (16.2 mL, 97.0 mmol), and the mixture was stirred at room temperature for 3 hr. The mixture was concentrated under reduced pressure and 6 mol/L hydrochloric acid was added thereto while cooling in ice, to adjust the pH to 4 to 5. A precipitated solid was collected by filtration to afford (4-tert-butylphenyl)acetic acid as a colorless powder (9.32 g).List of Compounds 1:...5-BENZYLOXYINDOLE-3-ACETIC ACID METHYL ESTERETHYL PYRIDINE-4-ACETATEMETHYL 4-TERT-BUTYLPHENYLACETATEETHYL MESITYLACETATE...General procedure: Aryl acetate 1a (2.0 mmol, 1.0 equiv.), CuO (0.2 mmol, 0.1equiv.) and aq TBHP (6.0 mmol, 3.0 equiv.) were added to aflask connected to a reflux condenser. The flask was heated at 110 C for 4.5 h and then cooled to room temperature.Pyridine (0.5 mL, 3.0 equiv.) was added and the mixture washeated to 50 C and stirred for 4.0 h. Thereafter, an aqueoussolution of Na2S2O3 (0.5 mol L-1, 10.0 mL) was added, andthe mixture was extracted with EtOAc (×3). The organiclayers were combined, washed with brine, dried overanhydrous Na2SO4, filtered, concentrated and purified byflash column chromatography over silica gel (200-300 mesh) using petroleum ether/EtOAc (25:1) to afford thedesired compound 2a (172.3 mg, 53% yield) as a colourlessoil.

Molecular Weight:206.28
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:206.130679813
Monoisotopic Mass:206.130679813
Topological Polar Surface Area:26.3
Heavy Atom Count:15
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes