1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone

1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone Property

Melting point:

108-109 °C(Solv: methanol (67-56-1))

Boiling point:

550.4±45.0 °C(Predicted)

Density 

1.206±0.06 g/cm3(Predicted)

pka

9.41±0.15(Predicted)

InChI

InChI=1S/C22H20O4/c1-16(23)22-20(24)12-19(25-14-17-8-4-2-5-9-17)13-21(22)26-15-18-10-6-3-7-11-18/h2-13,24H,14-15H2,1H3

InChIKey

HEHTYXOPJQUNOF-UHFFFAOYSA-N

SMILES

C(=O)(C1=C(OCC2=CC=CC=C2)C=C(OCC2=CC=CC=C2)C=C1O)C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone Chemical Properties,Usage,Production

Uses

1-(2,4-bis(Benzyloxy)-6-hydroxyphenyl)ethanone is a useful reactant for the synthesis of fluorine-containing chalcone derivatives that have antiproliferative activity.

Preparation

Preparation by reaction of benzyl chloride on phloroacetophenone with potassium carbonate in refluxing acetone (29%), (20%), in DMF at 100° (54%) and at 150–153° (26%) or in HMPA at 90–93° (80%).

Synthesis

The general procedure for the synthesis of 2-acetyl-3,5-bis(benzyloxy)phenol from 2',4',6'-trihydroxyacetophenone and benzyl chloride was as follows: to a solution of hexamethylphosphoramidite (HMPA, 300 mL) of 1-(2,4,6-trihydroxyphenyl)acetophenone (60 g, 0.36 mol) was added potassium carbonate (K2CO3, 148 g, 1.07 mol) and benzyl chloride (BnCl, 86.3 mL, 0.75 mol). The reaction suspension was stirred at 90 °C for 3 hours. After completion of the reaction, the solids were removed by filtration and the filtrate was poured into ice water. The pH of the mixture was adjusted to 2 by dropwise addition of dilute hydrochloric acid.Subsequently, the precipitated solid was collected by filtration and recrystallized in a solvent mixture of dichloromethane (CH2Cl2) and methanol (MeOH) to afford 1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)ethanone. The product yield was 75%; 1H NMR (CDCl3, 300 MHz) δ: 2.56 (3H, s), 5.06 (4H, s), 6.11 (1H, s), 6.17 (1H, s), 7.41 (10H, m), 14.04 (1H, s).

References

[1] Journal of Chemical Research - Part S, 1999, # 2, p. 148 - 149
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 488 - 490
[3] Synthesis, 2010, # 16, p. 2776 - 2786
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 8, p. 2864 - 2871
[5] Biochemical Pharmacology, 2014, vol. 92, # 2, p. 358 - 368