2-(Benzyloxy)benzaldehyde

Clear pale yellow liquid

Preparation : 2-(Benzyloxy)benzaldehycle To a stirred solution of sal ic 1 aldehyde (8.7mL, 81.8mmol) in acetonitrile (80mL) was added benzyl bromide (13.2mL, 90.07mmol) and K2CO3 (13.6g, 98.3mmol) at room temperature sequentially. The mixture was heated to reflux then stirred for 5hr. The resulting mixture was cooled to room temperature, filtered through celite, diluted with EtOAc, washed with water, dried over anhydrous MgS0. filtered and concentrated under reduced pressure. (17.4g, 80-100percent). 1H NMR (400 MHz, CDC13) δ 5.20 (s, 2H), 7.03-7.06 (m, 2H), 7.33-7.46 (m, 5H) , 7.52-7.56 (m, 1H), 7.85~7.88 (m, 1H) , 10.5 (d, J=0.40, 1H)General procedure: In a 100 mL roundbottomed flask equipped with a reflux condenser and a magneticstirring bar were dissolved 4-hydroxybenzaldehyde (35 g, 287 mmol) and 1-bromobutane (30.92 mL, 287 mmol) in DMF(750 mL). The mixture then was stirred under nitrogen for 20 min.Anhydrous potassium carbonate (118.83 g, 860 mmol) was thenadded and the mixture was stirred and heated at 70 °C under nitrogen.After 20 h, the reaction was allowed to cool to room temperature, treated with excess water, and extracted with ethylacetate. The combined organic extracts were then washed withwater several times and dried over anhydrous sodium sulfate, filtered. The crude productwas purified by chromatography (PE/EA, 20/1) yielding a brown oil. Yield: 95percent.Hydroxybenzaldehyde (1.0 mmol, 1.0 eq.) Was dissolved in anhydrous DMF (7 mL)And K2CO3 (1.5 mmol, 1.5 eq.) Was added to the stirred solution. The mixture was stirred at room temperature for 20 minutes. A drop benzyl bromide (1.2 mmol, 1.2 eq.) To the mixture and stirred for four hours at 40 .After completion of the reaction, it was cooled to room temperature, neutralized with 1N HCl and extracted with ether (3 x 25 mL). The combined organic solvent layers were washed with water (3 x 30 mL), brine (3 x 30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo.The crude compound was purified by column chromatography (EtOAc: Hexane = 1: 5-1: 4) to obtain the compound.A mixture of salicylaldehyde 1 (5.25 ml, 49.1 mmol) and benzyl bromide 2 (6.45 ml, 54.0 mmol) were added to asuspension of KTo a solution of salicylaldehyde (5.0 g, 41.0 mmol, 1.0 equiv) in acetone (125 mL) was added KLigand tris(2-hydroxy-benzyl)amine (L5)Ligand tris(o-hydroxy-benzyl)amine (L5) was synthesized by following reported procedure (Prins et al., 2006, Tet. Let. 47:2735).To a solution of 2-hydroxybenzaldehyde (49a) (3.98 mL, 38 mmol) in DMF (12mL)was added cesium carboniate (15.48 g, 47.5 mmol) and benzyl bromide (4.97 mL, 41.8mmol). The reaction mixture was stirred at room temperature for 36 h and quenched withcold water (50 mL). The solid obtained was collected by filtration washed with water (2 x50 mL) and dried under reduced pressure over P205 to furnish 2-benzyloxy)benzaIdehyde(49b)(6.524 g, 81 percent) as white solid; ‘H NMR (300 MHz, DMSO-c/6) 6 10.43 (d. J = 0.8Hz, [H), 7.75 -7.62 (in, 2H), 7.56-7.49 (in, 2H), 7.46 -7.30 (in, 4H), 7.10 (tt, J = 7.5, 0.9Hz, I H), 5.30 (s, 2H); MS (ES): MS (ES+) 235.2 (M+Na).2-Hydroxybenzaldehyde (645 μL, 5.5 mmol) was dissolved in 20 mL of DMF and K2CO3 (1.382 g, 10 mmol)And (bromomethyl) benzene (594 μL, 5 mmol) and heated to 50 ° C. The reaction was carried out for 1.5 hours, washed with saturated sodium carbonate solution until the aqueous phase was obtained colorless. Dried over magnesium sulphate and dried over silica gel to give a yield of 80percent.(Production of 2-Benzyloxybenzaldehyde) Salicylaldehyde (10.00 g, 81.88 mmol) was weighed.Benzyl chloride (15.55g, 122.83mmol) and potassium carbonate (22.63g, 163.77 mmol) was dissolved in 50 mL of DMF and reacted at 70 ° C for 6 h.After the TLC monitoring reaction was completed, 300 mL of water was added.Ethyl acetate(60mL × 3) extraction, the organic phase was combined, washed with brine, and evaporated to dryness under reduced pressure.Silica gel column chromatography (petroleum ether / ethyl acetate =60:1) Purified white solid 13.52 g, yield: 78percent, To a solution of aldehyde 5 (12.2 g, 0.10 mol) in ethanol (40 mL) a solution of benzyl chloride (13.9 g, 0.11 mol) in ethanol (50 mL) was added.

Molecular Weight:212.24
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:212.083729621
Monoisotopic Mass:212.083729621
Topological Polar Surface Area:26.3
Heavy Atom Count:16
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes