4-(BENZYLOXY)-3,5-DIMETHOXYBENZALDEHYDE

Benzyloxy-3, 5-dimethoxybenzaldehyde (5'-1)A solution of commercial aldehyde (6.0 g, 32.9 mmol) and benzyl bromide (5.9 mL, 49.4 mmol) in 70 mL of THF is added, in several fractions, to a solution of KOH (3.69 g, 65.8 mmol) in 40 mL of water. A catalytic quantity of BuGeneral procedure: To a solution of commercial available compound 3-methoxy-4-hydroxybenzaldehyde 9a (6.08 g, 40 mmol) in dry acetone (100 mL) was added BnBr (7.18 g, 42 mmol) and KAdd 3, 5-dimethoxy-4-hydroxybenzaldehyde to a 250ml single-mouth bottle(P61, 7g, 38.42 mmol), benzyl bromide (7.89 g, 46.11 mmol), K2CO3 (6.37 g, 46.11 mmol) and 50 m DMF (ie, N, N-Dimethylformamide) was stirred at room temperature for 18 hours and was poured into 500 ml of ice water after completion of the reaction. The resulting precipitate filters, waterWash (3x20ml0, 9.5g (90.8percent) of yellow powder after dryingTo a stirring suspension of syringaldehyde (25.19 g, 138 mmol) and potassium carbonate (38.14 g, 276 mmol, 2 equ) in N, N-dimethyl formamide (500 ml) was added benzyl bromide (20 ml, 168 mmol, 1.2 equ). The reaction was stirred for 25 hours, then poured into dichloromethane. The organic solvent was washed with water [(5X)] then dried [(MGSO4)] and concentrated in vacuo to give a pink oil. This was recrystallised from hexane to give 31 (32.9 g, 87 percent). [APOS;H] nmr (400 MHz, CDC13) 3.92 (s, 6H) 5.15 (s, 2H) 7.13 (s, 2H) 7.28-7. 38 (m, 3H) 7.48 (d, 2H, 7.4 Hz) 9.91 (s, [1H). 13C NMR] (100 MHz, CDC13) 56.638 (CH3) 75.428 (CH2) 105.085 (CH) 128.479 (CH) 128.615 (CH) 128.803 (CH) 132.286 (Q) 137.591 (Q) 142.790 (Q) 154.384 (Q) 191. [491] (CH). EI+ 272.0 (15 percent) M, 91.1 (100 [percent)] Bn. [C16H1S04] calc. [272. 1049, ] obs. 272.1053. mp 56-57 [°C]

Molecular Weight:272.29
XLogP3:2.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:272.10485899
Monoisotopic Mass:272.10485899
Topological Polar Surface Area:44.8
Heavy Atom Count:20
Complexity:274
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes