2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10583334, compound

To an aqueous solution of 10-((4-methoxybenzyl)oxy)-1-decene-3-ol (590 mg, 2.02 mmol, 1.00 eq.) in methylene chloride (20.0 mL) and saturated sodium bicarbonate (10.0 mL), was added DDQ (687 mg, 3.03 mmol, 1.50 eq.) at room temperature. The mixture was allowed to react at the same temperature for 5 hours, and then the reaction solution was poured into 10% aqueous sodium thiosulfate solution. The organic phase was extracted with ethyl acetate, and then the resulting organic phase was washed with 10% aqueous sodium thiosulfate solution, a saturated aqueous sodium bicarbonate solution, and a saturated salt solution. The washed organic phase was dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=70:30) to obtain 1-decene-3,10-diol as shown below (324 mg, 1.88 mmol, 93%).

1. customto react at the same temperature for 5 hours
2. extractionThe organic phase was extracted with ethyl acetate
3. washthe resulting organic phase was washed with 10% aqueous sodium thiosulfate solution
4. dry with materialThe washed organic phase was dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=70:30)

ORD record

ord-3170f7e36fbb41679f8c605ad5274e83

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073802B2