Chloromethyl Methyl Ether → 4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenol

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Reaction Steps

2-Propyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenylacetate (13.67 g, 39.7 mmol) in dichloromethane (160 mL) was added with N,N-diisopropylethylamine (27.6 mL) and then with chloromethyl methyl ether (6.0 mL). The resultant mixture was stirred at 40° C. for 18 hours, added with methanol at room temperature (20 mL), stirred for 1.5 hours, then added with potassium carbonate (11 g, 39.7 mmol), and stirred overnight. The reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (10.87 g, yield 79%) was obtained as a pale yellow oil.

Provenance & Evidence