4-(4-ethylphenyl)butanoicacid

To a solution of mercuric chloride (666 mg, 2.45 mmol) in water (7 mL) and concentrated HC1 (20 mL) was slowly added zinc (6.66 g, 102 mmol). After bubbling subsided, additional portions of mercuric chloride (666 mg, 2.45 mmol) and zinc (6.66 g, 102 mmol) were added. The contents were stirred for 30 minutes at roomtemperature. The liquid was decanted, and the solid amalgam was washed twice with water. A solution of 4-(4-ethylphenyl)-4-oxobutyric acid (3.00 g, 14.5 mmol) in toluene (7.5 mL), water (15 mL), and concentrated HC1 (15 mL) was then added to the mercury-zinc amalgam. The mixture was heated at reflux for 17 hours, then filtered. The filtrate was diluted with EtOAc (200 mL) and washed with brine (100 mL). The organic phase was dried over anhydrous Na SCL and concentrated under reduced pressure. Purification by flash column chromatography (DCM to 25:75 DCM/EtOAc) afforded 41 as a white solid (2.04 g, 73% yield). Rf= 0.27 (DCM/EtOAc 50:50 v/v).1H NMR (400 MHz, DMSO-r6) delta 12.03 (br s, 1H), 7.11 (d, J= 8.2 Hz, 2H), 7.08 (d, J = 8.2 Hz, 2H), 2.60-2.48 (m, 4H), 2.20 (t, J= 7.4 Hz, 2H), 1.77 (app quint, J= 7.5 Hz, 2H), 1.16 (t, J= 7.6 Hz, 3H).13C NMR (101 MHz, DMSO-d6) delta 174.3, 141.1, 138.7, 128.2, 127.7, 34.0, 33.1, 27.8, 26.4, 15.7. MS (ESI+) calculated for [Ci2Hi50]+[M-OH]+, 175.1; found 175.1.B. STAGE B 4-(4-ETHYLPHENYL)BUTYRIC ACID STR52 In a 100-cm3 flask, 2.5 g of 4-oxo-4-(4-ethylphenyl)butyric acid are dissolved with magnetic stirring in 19 cm3 of trifluoroacetic acid. 3.2 g of triethylsilane are added dropwise. The reaction mixture is stirred for 86 hours at room temperature. It is poured into ice. It is extracted with 3 volumes of ether. The organic phases are washed 3 times with 10% potassium carbonate solution. The aqueous phases are combined and then acidified by adding concentrated hydrochloric acid until the pH is 3-4. The precipitate obtained is drained and then recrystallized. Infrared spectroscopic analysis: 3280-2780 cm-1: nu acid OH 2940-2850 cm-1: nu alkyl CH 1680 cm-1: nu acid CO 1510 cm-1: nu aromatic C=C

Molecular Weight:192.25
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:192.115029749
Monoisotopic Mass:192.115029749
Topological Polar Surface Area:37.3
Heavy Atom Count:14
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes