4-BENZYLOXY-2-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

98-100°C

Boiling point:

180°C 2mm

Density 

1.154±0.06 g/cm3(Predicted)

Flash point:

180°C/2mm

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light yellow to brown Solid

Sensitive 

Air Sensitive

BRN 

1880700

CAS DataBase Reference

58026-14-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

HS Code 

2912490090

MSDS

• Language:English Provider:ALFA

4-BENZYLOXY-2-METHOXYBENZALDEHYDE Usage And Synthesis

Synthesis

4-Hydroxy-2-methoxybenzaldehyde (200 mg, 1.31 mmol) was dissolved in N,N-dimethylformamide (DMF) under the protection of nitrogen (N2), potassium carbonate (K2CO3, 543 mg, 3.93 mmol) was added, and stirred for 30 min at room temperature. Subsequently, benzyl bromide (BnBr, 0.312 mL, 2.62 mmol) was added dropwise to the reaction mixture and stirring was continued for 1.5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc) and washed with deionized water (H2O). The organic phase was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. Purification by silica gel column chromatography with ethyl acetate/hexane (1:2, v/v) as eluent afforded the target product 4-benzyloxy-2-methoxybenzaldehyde (304 mg, 95.7% yield).1H-NMR (CDCl3, 400 MHz) δ: 7.81 (d, 1H, J = 8.6 Hz), 7.36 (m, 5H), 6.62 ( dd, 1H, J = 8.7, 2.2 Hz), 6.54 (d, 1H, J = 2.2 Hz), 5.14 (s, 2H), 3.89 (s, 3H).

References

[1] Molecules, 2015, vol. 20, # 9, p. 15966 - 15975
[2] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 9, p. 1429 - 1437
[3] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10640 - 10641
[4] Patent: WO2006/40520, 2006, A1. Location in patent: Page/Page column 103
[5] Patent: WO2007/99326, 2007, A1. Location in patent: Page/Page column 111

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