| Identification | More | [Name]
3,5-Dibenzyloxyacetophenone | [CAS]
28924-21-2 | [Synonyms]
3',5'-BIS(BENZYLOXY)ACETOPHENONE 3',5'-DIBENZYLOXYACETOPHENONE 3,5-DIBENZYLOXYACETOPHENONE 3',5'-DIBENZYLOXYACETPHENONE 1-[3,5-bis(phenylmethoxy)phenyl]-ethanon 3',5'-Dibenzyloxyacetophenone 3,5-Dibenzyloxyacetophenone (3,5-BIS-BENZYLOXY-PHENYL)-METHANOL Terbutaline3,5-DibenzylOxyAcetophenone 3,5-Dibenxyloxyacetophenone 3',5'-Dibenzyloxyacetophenone 98% 1-[3,5-bis(benzyloxy)phenyl]ethanone Ethanone, 1-[3,5-bis(phenylmethoxy)phenyl]- 1-[3,5-Bis(phenylmethoxy)phenyl]ethanone | [EINECS(EC#)]
249-315-7 | [Molecular Formula]
C22H20O3 | [MDL Number]
MFCD00004777 | [Molecular Weight]
332.39 | [MOL File]
28924-21-2.mol |
| Chemical Properties | Back Directory | [Appearance]
beige crystalline powde | [Melting point ]
60-62 °C (lit.) | [Boiling point ]
429.52°C (rough estimate) | [density ]
1.1079 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in dichloromethane, ethyl acetate and methanol | [form ]
Solid | [color ]
Off-White to Pale Yellow | [InChI]
InChI=1S/C22H20O3/c1-17(23)20-12-21(24-15-18-8-4-2-5-9-18)14-22(13-20)25-16-19-10-6-3-7-11-19/h2-14H,15-16H2,1H3 | [InChIKey]
KOJXGMJOTRYLBD-UHFFFAOYSA-N | [SMILES]
C(=O)(C1=CC(OCC2=CC=CC=C2)=CC(OCC2=CC=CC=C2)=C1)C | [CAS DataBase Reference]
28924-21-2(CAS DataBase Reference) | [EPA Substance Registry System]
28924-21-2(EPA Substance) |
| Questions And Answer | Back Directory | [Preparation]
Over 1.5 hours, methyllithium (531 mL 2 mol solution, 1.06 M) was added to a rapidly stirred solution of 3,5-dibenzyloxybenzoic acid (175 g, 0.532 M) in diethyl ether (250 mL) and tetrahydrofuran (1400 mL) at 15°–20°C. After stirring for another 0.75 hours at 10°–15°C, water (600 mL) was slowly added, maintaining the reaction temperature below 20°C. The aqueous layer was separated and extracted with diethyl ether (3 × 250 mL). The combined organic phases were washed with saturated sodium chloride solution (4 × 300 mL), dried over sodium sulfate, and concentrated under vacuum to give an oil that slowly crystallized from isopropyl ether. The crude product was recrystallized from diethyl ether-hexane to give 104.7 g. (59%) 3,5-Dibenzyloxyacetophenone; melting point 59°-61° C. |
| Hazard Information | Back Directory | [Chemical Properties]
beige crystalline powde | [Uses]
3,5-Dibenzyloxyacetophenone is used in the synthesis of enantiomerically pure B-ring modified analogs of (-)-epicatechin gallate. | [References]
[1] Ganapati D. Yadav, Omprakash V. Badure. “Selective acylation of 1,3-dibenzyloxybenzene to 3,5-dibenzyloxyacetophenone over cesium modified dodecatungstophosphoric acid (DTP) on clay.” Applied Catalysis A: General 348 1 (2008): Pages 16-25. |
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