ChemicalBook CAS DataBase List 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)ethanone

1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)ethanone synthesis

8synthesis methods

Product Name:1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)ethanone
CAS Number:65490-09-7
Molecular formula:C12H16O6
Molecular Weight:256.25

Obtained by reaction of methoxymethyl chloride with phloroacetophenone in the presence of potassium carbonate,.

109-87-5
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480-66-0 Synthesis

2',4',6'-Trihydroxyacetophenone monohydrate

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1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)ethanone

65490-09-7
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Yield:65490-09-7 100%

Reaction Conditions:

Stage #1: Dimethoxymethanewith acetyl chloride;zinc dibromide in dichloromethane at 20 - 30; for 3.5 h;
Stage #2: 2,4,6-trihydroxyacetophenonewith N-ethyl-N,N-diisopropylamine in dichloromethane at 5 - 10;

Steps:

35 5.1.35. 1-[2-Hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone (49)

To a stirred solution of dimethoxymethane (66 mL, 745 mmol)and zinc bromide (447 mg, 1.12 mmol) in DCM (580 mL) wasadded dropwise acetyl chloride (53 mL, 745 mmol) during 30 minmaintaining the temperature below 30 C. After stirring 3 h atroom temperature, the solution was diluted with DCM (1.2 L), thencooled at 5 C before the portion wise addition of 1-(2,4,6-trihydroxyphenyl)ethanone (48, 50.0 g, 298 mmol) followed by the dropwiseaddition of N,N-diisopropylethylamine (208 mL, 1.19 mol).After 1 h the ice bath was removed and the temperature was allowedto rise to room temperature. The resulting cloudy solutionwas stirred overnight, and then was washed with NH4Cl saturatedsolution, followed by washing with 10% citric acid solution. Afterdrying over Na2SO4, the solvent was removed to give 49 (78.0 g,100%). 1H NMR (400 MHz, DMSO-d6) d 13.31 (s, 1H), 6.24 (d,J = 2.3 Hz, 1H), 6.19 (d, J = 2.3 Hz, 1H), 6.19 (d, J = 2.3 Hz, 1H),5.30 (s, 2H), 5.22 (s, 2H), 3.44 (s, 3H), 3.38 (s, 3H), 2.60 (s, 3H);LC-MS (ESI): m/z 257 [M+H]+; HRMS (ESI): m/z calcd forC12H16O6+H+ 257.1020, found 257.1019.

References:

Brasca, Maria Gabriella;Mantegani, Sergio;Amboldi, Nadia;Bindi, Simona;Caronni, Dannica;Casale, Elena;Ceccarelli, Walter;Colombo, Nicoletta;De Ponti, Anna;Donati, Daniele;Ermoli, Antonella;Fachin, Gabriele;Felder, Eduard R.;Ferguson, Ronald D.;Fiorelli, Claudio;Guanci, Marco;Isacchi, Antonella;Pesenti, Enrico;Polucci, Paolo;Riceputi, Laura;Sola, Francesco;Visco, Carlo;Zuccotto, Fabio;Fogliatto, Gianpaolo [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 22,p. 7047 - 7063]

480-66-0 Synthesis

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