2-ETHYLBENZYLALCOHOL98

A solution of compound 28 (70.0 g, 466 mmol) in dry THF (500 mL) was treated with 10 M solution of BH3in THF (53 mL, 53.0 mmol of BH3) at 0C. The reaction mass was stirred at r.t. for 24h before methanol (150 mL) was slowly added thereto. The resulting mixture was stirred for 45 min, and evaporated under reduced pressure to yield 55.0 g (404 mmol, 87%) of compound 29, pure enough for the next step.A solution of compound 28 (70.0 g, 466 mmol) in dry THF (500 mL) was treated with 10 M solution of BH3 in THF (53 mL, 53.0 mmol of BH3) at 0C. The reaction mass was stirred at r.t. for 24h before methanol (150 mL) was slowly added thereto. The resulting mixture was stirred for 45 mm, and evaporated under reduced pressure to yield 55.0 g (404 mmol, 87%) ofcompound 29, pure enough for the next step.0.30 g (2 mmol, 1.0 eq) 38 2-ethyl-benzoic acid (compound 12a) was dissolved in 16 ml anhydrous 39 THF, then 4 ml (4 mmol, 2.0 eq) 1M 40 BH3/THF solution was added dropwise under the condition of ice bath. After reacting at room temperature for 3.0 hours, THF was removed by vacuum distillation. 1 M HCl (41 aq) was added in the reaction system under the condition of ice water bath until no more air bubble came out. Then water and EA(10 ml*2) were added for extract and the organic phase was washed twice with saturated sodium bicarbonate solution and then twice with saturated sodium chloride solution.The solution was dried over anhydrous sodium sulfate and desolventlized to gain light yellow oily material (Compound 13g). The crude product was used without purification in the next step directly. 42 Benzyl alcohol intermediate compound 13h to 13m can be obtained with the same reduction method from compound 12b to 12g.General procedure: To a solution of benzoic acids 16a-16e (2 mmol) in anhydrous THF (16 ml) was added the solution of BH3 in THF (4 ml, 4 mmol) slowly at 0 C. The reaction mixture was stirred at room temperature for 3.0 h. After the organic solvent was evaporated, the residual was extracted by ethyl acetate. The extract was washed with NaHCO3 (aq), brine and dried over Na2SO4. The organic layer was condensed and the crude product was obtained as light yellow oils. The 17e-17i were used directly for the next step without further purification. (2-ethylphenyl)methanol 17e, yield 80.4%, ESI-MS(m/z): 137.1[M+H]+.

Molecular Weight:136.19
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:136.088815002
Monoisotopic Mass:136.088815002
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:90.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes