HCID 66743536, compound → 4-(2,3-Dimethoxyphenyl)butanoic acid

Participants

Reaction Steps

Acid 5 (3.7 g, 0.017 mol) was dissolved in 25 mL absolute EtOH and added to a Parr hydrogenation bottle containing 0.6 g of 10% Pd/C. The bottle was then pressurized to 25 psi H2 and shaken for 2 h. The contents were then filtered through Celite, the solvents were evaporated, and the resulting oil dried under high vacuum to yield a grey solid (3.7 g, 0.017 mol, quant. yield). The solid was recrystallized from EtOAc/hexanes to produce fine white needles; mp 58-59° C. (lit.27 mp 58.5-60° C.). 1H NMR: (300 MHz, CDCl3): δ 6.97 (t, 1H, J=8 Hz, ArH); 6.76 (d, 1H, J=8 Hz, ArH); 6.75 (d, 1H, J=8 Hz, ArH); 3.84 (s, 3H, ArOCH3); 3.80 (s, 3H, ArOCH3); 2.67 (t, 2H, J=7 Hz, HO2CCH2CH2); 2.37 (t, 2H, J=7 Hz, ArCH2); 1.92 (p, 2H, J=7 Hz, HO2CCH2CH2). ESIMS (M+Na+)=247.

Provenance & Evidence