3-HYDROXY-4-BENZYLOXY BENZALDEHYDE Chemical Properties

Melting point:

120 °C(Solv: ethanol (64-17-5))

Boiling point:

403.3±30.0 °C(Predicted)

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

8.79±0.35(Predicted)

color 

Off-White to Light Brown

InChI

InChI=1S/C14H12O3/c15-9-12-6-7-14(13(16)8-12)17-10-11-4-2-1-3-5-11/h1-9,16H,10H2

InChIKey

HUNGEAFDVLSPAM-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(OCC2=CC=CC=C2)C(O)=C1

CAS DataBase Reference

4049-39-2

3-HYDROXY-4-BENZYLOXY BENZALDEHYDE Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

4-Benzyloxy-3-hydroxybenzaldehyde is useful for preparing quinazoline derivatives.

Synthesis

To a solution of 3,4-dihydroxybenzaldehyde (2.03 g, 14.7 mmol) in acetone (150 mL) was added potassium carbonate (K2CO3, 3.05 g, 22.1 mmol) and benzyl bromide (1.74 mL, 14.7 mmol). The reaction mixture was stirred under reflux conditions for 4 hours. Upon completion of the reaction, the reaction mixture was filtered through Celite? 535RVS and the filtrate was subsequently concentrated under reduced pressure. The residue was purified by column chromatography using toluene/ethyl acetate (13:1, v/v) as eluent to afford 4-(benzyloxy)-3-hydroxybenzaldehyde (2.12 g, 63% yield) as colorless prismatic crystals. The product characterization data were as follows: 1H NMR (300 MHz, CDCl3) δ 5.21 (2H, s), 5.77 (1H, s), 7.05 (1H, d, J = 8.2 Hz), 7.37-7.43 (7H, m), 9.86 (1H, s); 13C NMR (75 MHz, CDCl3) δ 71.2, 111.5, 114.4, 124.4, 127.9, 128.8, 128.9, 130.8, 135.2, 146.3, 150.9, 191.0; IR (ATR) νmax 3201, 1671, 1604, 1577, 1511, 1454, 1389, 1343, 1283, 1165, 1151, 1015 , 962, 874, 811, 786, 738, 698, 678 cm-1; EIMS m/z (relative intensity) 228 [M]+ (40), 91 (100); HR-EIMS m/z: [M]+ calculated C14H12O3 228.0786, measured 228.0789; melting point 120.0-122.0°C.

References

[1] Patent: WO2014/149793, 2014, A1. Location in patent: Page/Page column 59-60; 93; 96
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 22, p. 4693 - 4711
[3] Chemistry - A European Journal, 1998, vol. 4, # 1, p. 33 - 43
[4] Journal of Natural Products, 2018, vol. 81, # 2, p. 371 - 377
[5] Organic Letters, 2012, vol. 14, # 15, p. 3902 - 3905

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