4,4',4''-(benzene-1,3,5-triyltris(ethyne-2,1-diyl))tribenzoic acid synthesis

Yield: 97%

Reaction Conditions:

Stage #1:C₃₆H₂₄O₆ with lithium hydroxide monohydrate;water in tetrahydrofuran at 20; for 16 h;
Stage #2: with hydrogenchloride in waterCooling with ice;

Steps:

A mixture of trimethyl 4,4',4"-(benzene-l,3,5-triyltris(ethyne-2, l-diyl))tribenzoate (773 mg, 1.40 mmol), LiOH-H₂0 (881 mg, 21.0 mmol), tetrahydrofuran (THF, 25 mL) and water (5 mL) was stirred for 16 h at room temperature. The reaction mixture was concentrated. The residue was acidified with cold 3 M HCl (1 M = 1 mol dm^-3) and cooled in an ice bath. The precipitate was filtered and washed with cold 3 M HCl. The ivory solid was dried. The dried solid was taken up in THF and filtered to remove insoluble inorganic salt. The solution was dried over MgS0₄, filtered concentrated and dried under vacuum to give an ivory solid (693 mg, 97%): mp 352 °C;-NMR (DMSO-d6, 400 MHz) δ 8.01 (d, 6H, J = 8.0 Hz), 7.88 (s, 3H), 7.72 (d, 6H, J = 8.0 Hz); ¹³C-NMR (DMSO-d6, 100 MHz) δ 166.6, 134.5, 131.8, 131.0129.6, 126.0, 123.4, 90.3, 89.8; FT-IR (KBr, 4000-400 cm^-1) 3428 (br), 2994 (br), 2658 (w), 2534 (w), 2376 (w), 1687 (s), 1604 (s), 1518 (s), 1312 (s), 1277 (s), 1173 (w), 1105 (w), 856 (m), 768 (s); MALDI-TOF MS (m/z) [M]+ 510.0935 (found), 510.1103 (calcd. for

References:

THE REGENTS OF THE UNIVERSITY OF CALIFORNIA;FOUNDATION OF SOONGSIL UNIVERSITY-INDUSTRY COOPERATION;YAGHI, Omar, M.;FURUKAWA, Hiroyasu;KIM, Jaheon;KO, Nakeun;CHOI, Sang, Beom WO2011/38208, 2011, A2 Location in patent:Page/Page column 33