| Identification | Back Directory | [Name]
1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone | [CAS]
18065-05-9 | [Synonyms]
2-Acetyl-3,5-bis(benzyloxy)phenol
1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone
Ethanone, 1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]- | [Molecular Formula]
C22H20O4 | [MOL File]
18065-05-9.mol | [Molecular Weight]
348.39 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [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 |
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