2',4'-Dihydroxyacetophenone → 1-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone

In 60 ml of dimethylformamide were dissolved 5.0 g of 2',4'-dihydroxyacetophenone and 6.37 g of N,N-diisopropylethylamine, and 2.72 ml of chloromethyl methyl ether was gradually added to the solution under ice cooling. The mixture was stirred under ice cooling for 20 minutes and a reaction was carried out at room temperature for 1.5 hours. After the reaction, the reaction mixture was extracted with 300 ml of diethyl ether, and the diethyl ether layer was washed with water (100 ml×2 times), shaken with a saturated aqueous solution of sodium chloride (50 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation and the residue was subjected to the silica gel chromatography (3.5 cm in diameter; 72.8 g; n-hexane/ethyl acetate=4/1; 0.3 kg/cm2) to obtain 5.66 g (yield=87.8%) of 2'-hydroxy-4'-methoxymethoxyacetophenone in the form of a colorless oil.

1. additionwas gradually added to the solution under ice cooling
2. waita reaction was carried out at room temperature for 1.5 hours
3. customAfter the reaction
4. extractionthe reaction mixture was extracted with 300 ml of diethyl ether
5. washthe diethyl ether layer was washed with water (100 ml×2 times)
6. stirringshaken with a saturated aqueous solution of sodium chloride (50 ml×2 times)
7. dry with materialdried with anhydrous sodium sulfate
8. filtrationfiltered
9. customThe solvent was removed from the filtrate by distillation

ORD record

ord-97659357705d4d3e9e515f6f4deb2598

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05234951