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To a solution of 86.4 mg (159.78 μmol) 3-(3′-Benzyl-4″-(cyanomethoxy)-2,3″-diisobutyl-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (57) in 6 ml methanol and 6 ml THF 3 ml (24.90 mmol, 155 eq.) 25% aq. NaOH-solution was added. The resulting mixture was refluxed for 24 h and then cooled to 0° C. After acidifying to pH 2 by adding 1 N aq. HCl-solution brine was added and the mixture was extracted with THF. The comb. org. fractions were washed twice with brine, dried over MgSO4 and evaporated. Column chromatography (first CH2Cl2/MeOH (4+1), then EtOAc/HOAc (95+5)) yielded 70.9 mg (122.5 μmol, 76.67%) 3-(3′-Benzyl-4″-(carboxymethoxy)-2,3″-diisobutyl-1,1′:4′,1″-terphenyl-4-yl)propanoic acid (58) as a white solid. Rf (EtOAc/HOAc (95+5))=0.76. 1H-NMR (500 MHz, d4-MeOH+1% d4-HOAc): δ=0.83 (d, 6H, J=6.62 Hz, 2*CH3), 1.02 (d, 6H, J=6.62 Hz, 2*CH3), 1.76 (m, 1H, CH), 2.07 (m, 1H, CH), 2.60 (d, 2H, J=7.25 Hz, CH2), 2.68 (d, 2H, J=7.25 Hz, CH2), 2.77 (t, 2H, J=7.57 Hz, CH2CH2CO2H), 3.06 (t, 2H, J=7.57 Hz, CH2CH2CO2H), 4.14 (s, 2H, CH2Ph), 4.79 (s, 2H, OCH2CO2H), 6.99 (d, 1H, J=8.36 Hz), 7.10 (m, 2H), 7.21-7.33 (m, 10H), 7.39 (d, 1H, J=7.72 Hz). 13C-NMR (125 MHz, d4-MeOH+1% d4-HOAc): δ =20.89, 22.85, 23.04, 29.82, 30.66, 30.92, 31.78, 35.38, 36, 89, 40.01, 40.52, 44.83, 112.38, 126.21, 126.74, 126.81, 128.36, 128.88, 129.30, 129.76, 131.08, 131.17, 131.31, 132.74, 133.18, 135.33, 139.16, 140.26, 140.92, 141.37, 141.81, 142.40, 143.14, 156.93, 160.58, 171.38, 178.30. MS (ESI): 580 (10), 579 (42), 578 (100), 326 (10), 312 (19), 289 (26), 260 (15), 186 (12), 173 (10). HR-MS (FAB): Calcd. for C38H42O5: 578.303225. Found: 578.303100.

1. temperatureThe resulting mixture was refluxed for 24 h
2. additionwas added
3. extractionthe mixture was extracted with THF
4. washfractions were washed twice with brine
5. dry with materialdried over MgSO4
6. customevaporated