Hydrochloric Acid → (3,5-Di-tert-butylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

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; 1H-NMR (CDCl3) δ1.33 (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).

Provenance & Evidence