2',5'-dihydroxyoctanophenone synthesis
- Product Name:2',5'-dihydroxyoctanophenone
- CAS Number:4693-19-0
- Molecular formula:C14H20O3
- Molecular Weight:236.31
Yield:4693-19-0 73.2%
Reaction Conditions:
with boron trifluoride dihydrate at 90; for 0.333333 h;Microwave irradiation;
Steps:
2.2.1. General procedure for the synthesis of acylhydroquinones 3-20
General procedure: The synthetic methodology to obtain the studied compounds 3-20 isdepicted in Scheme 1. The already reported methodology of obtentionof acylhydroquinones [30] was improved using microwave irradiationat 90 °C, at a fixed power of 150 W as follows. To a 10 mL CEM microwaveprocess vial equipped with a stir bar were added one equivalentof hydroquinone, 1.5 equivalent of carboxylic acid and 4 mL ofBoron trifluoride dihydrate. The mixture was irradiated under microwaveby 20 min. The mixture was allowed to cool to room temperature,extracted with ethyl acetate, the extract washed with distilled waterand dried with anhydrous sodium sulfate, then was filtered and concentratedunder vacuum. Afterward, the corresponding acylhydroquinonewas purified by flash chromatography with hexane/ethylacetate 4:1 as eluent. in this manner were obtained the acylhydroquinones3-11. Compounds 12-20 were obtained by chlorination,with hydrogen chloride, of the respective quinones obtained by oxidationof the hydroquinones 3-11, with Ag2O in dichloromethane [26],these compounds also were purified by flash chromatography withhexane/ethyl acetate 4:1 as eluent. The 1H NMR and 13C NMR spectradata for acylhydroquinones 3-20 are provided in the supplementaryinformation.
References:
Aguilera, Renato J.;Araya-Maturana, Ramiro;Borrego, Edgar A.;Carrillo, Ileana;Chávez-Báez, Ignacio;Correa, Pablo;Donoso-Bustamante, Viviana;Fuentes-Retamal, Sebastián;Gutiérrez, Denisse A.;Millas-Vargas, Juan Pablo;Miranda, Dante;Pulgar, Rodrigo;Schiaffino-Bustamante, Yareli;Urra, Félix A.;Varela-Ramírez, Armando [Bioorganic Chemistry,2020,vol. 100]
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