3,4-BIS(BENZYLOXY)BENZOIC ACID Chemical Properties

Melting point:

182 °C

Boiling point:

512.7±40.0 °C(Predicted)

Density 

1.232±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly, Heated), DMSO (Slightly)

form 

Solid

pka

4.31±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C21H18O4/c22-21(23)18-11-12-19(24-14-16-7-3-1-4-8-16)20(13-18)25-15-17-9-5-2-6-10-17/h1-13H,14-15H2,(H,22,23)

InChIKey

BYOKJLCIKSFPDU-UHFFFAOYSA-N

SMILES

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

3,4-BIS(BENZYLOXY)BENZOIC ACID Usage And Synthesis

Uses

3,4-Bis(phenylmethoxy)-benzoic Acid is a useful synthetic intermediate. It is an intermediate used to synthesize Jaboticabin (J210370) which is minor bioactive depside potent to treat chronic obstructive pulmonary disease.

Synthesis

C) Synthesis of 3,4-dibenzyloxybenzoic acid: Sodium hydroxide (1.2 g) was dissolved in methanol (100 mL) to prepare a methanolic solution of sodium hydroxide. This solution was added to a solution of methanol (50 mL) containing methyl 3,4-dibenzyloxybenzoate (4.64 g), and the reaction mixture was heated under reflux for 4 hours. After completion of the reaction, the methanol was evaporated under reduced pressure. The residue was dissolved in water (100 mL) and the aqueous layer was washed with ethyl acetate (2 x 50 mL). Subsequently, the aqueous layer was acidified to pH 2 with 2N hydrochloric acid, whereupon 3,4-dibenzyloxybenzoic acid precipitated as a precipitate. The precipitate was collected by filtration and dried under vacuum to give 2.4 g of 3,4-dibenzyloxybenzoic acid in 74% yield. The product was characterized by 1H NMR (CDCl3): δ 7.7 (2H, br s), 7.27-7.5 (10H, m), 6.98 (1H, d, J=8 Hz), 5.26 (2H, s), 5.22 (2H, s).

References

[1] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1411 - 1415
[2] Patent: WO2005/113489, 2005, A1. Location in patent: Page/Page column 90
[3] European Journal of Medicinal Chemistry, 1997, vol. 32, # 5, p. 409 - 423
[4] Heterocycles, 2014, vol. 8, # 2, p. 1371 - 1396
[5] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 24 - 33

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