3,5-Bis(1,1-dimethylethyl)benzoic acid

White powder

6 (2E, 4E, 6E)-7-(3, 5-Di-t-butylphenyl)-3-methyldeca-2, 4, 6-trienoic acid (27) and (2E, 4E, 6Z)-7-(3, 5-di-t-butylphenyl)-3-methyldeca-2, 4, 6-trienoic acid (28), prepared according to Scheme 4 illustrated and described below. STR9 3, 5-Di-t-butylbenzyl alcohol (17). To 10.0 g (42.7 mmol) of acid 1 in 20 niL of dry THF at 0 C. was added 42.7 mL (42.7 mmol) of LAH (1.0 M in THF). The reaction mixture was warmed to 50 C. and stirred for 15 min. After cooling the reaction to RT, 20% aqueous HCI was added until the solution turned clear. The solution was extracted with EtOAc (2*50 mL), and the combined EtOAc extract was washed (water, then brine), dried (MgSO4), filtered and concentrated to give 8.8 g (40.0 mmol) of 17 (94% yield): The product was directly used in the next step. TLC (20% EtOAc-80% hexanes) Rf 0.4; 1 H-NMR (CDCl3)delta 1.33 (s, 18H, 6(CH3)), 4.68 (s, 2H, CH2) 7.22 (d, J=1 Hz, 2H, Ar--H), 7.38 (t, J=1 Hz, 1H, Ar--H).3, 5-Di-t-butylbenzyl alcohol (17). To 10.0 g (42.7 mmol) of acid 1 in 20 mL of dry THF at 0 C. was added 42.7 mL (42.7 mmol) of LAH (1.0M in THF). The reaction mixture was warmed to 50 C. and stirred for 15 min. After cooling the reaction to RT, 20% aqueous HCl was added until the solution turned clear. The solution was extracted with EtOAc (2*50 mL), and the combined EtOAc extract was washed (water, then brine), dried (MgSO4), filtered and concentrated to give 8.8 g (40.0 mmol) of 17 (94% yield): The product was directly used in the next step. TLC (20% EtOAc-80% hexanes) Rf 0.4; 1 H-NMR (CDCl3) delta1.33 (s, 18H, 6(CH3)), 4.68 (s, 2H, CH2) 7.22 (d, J=1 Hz, 2H, Ar-H), 7.38 (t, J=1 Hz, 1H, Ar-H).3, 5-Di-t-butylbenzoic acid (5.00 g, 0.021 mol) was dissolved in anhydrous THF (250 mL) under argon atmosphere and the solution cooled to 0 C. Lithium aluminum hydride (1.62 g, 0.043 mol) was added in small portions and the solution stirred at room temperature overnight. The reaction was quenched with water, Et2O (100 mL) was added and the mixture acidified with concentrated HCl solution until the solid residue was dissolved. The medium was extracted with Et2O and the organic phase dried over MgSO4, filtered and concentrated to yield 4.31g of 5a. 1H NMR delta (CDCl3) 1.34 (s, 18H, di-t-butyl), 4.70 (s, 2H, PhCH2OH), 7.23 (d, 2H, J = 1.8 Hz, 2-CH and 6-CH), 7.38 (t, 1H, J = 1.8 Hz, 4-CH).

Molecular Weight:234.33
XLogP3:4.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:234.161979940
Monoisotopic Mass:234.161979940
Topological Polar Surface Area:37.3
Heavy Atom Count:17
Complexity:258
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes