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

HRID 1919755Notes

Reaction equation

C(N(CC)C(C)C)(C)C.C([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=1[CH2:30][CH2:31][CH3:32])(=O)C.[CH3:33][O:34][CH2:35]Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.CO>[F:26][C:25]([F:28])([F:27])[C:20]([C:17]1[CH:18]=[CH:19][C:14]([OH:13])=[C:15]([CH2:30][CH2:31][CH3:32])[CH:16]=1)([O:29][CH2:33][O:34][CH3:35])[C:21]([F:23])([F:24])[F:22]

Participants

Conditions

Temperature: 40 °C

Procedure

N,N-Diisopropylethylamine (27.6 mL) was added to 2-propyl-4-[1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl]phenyl acetate (13.67 g, 39.7 mmol) in dichloromethane (160 mL), and then chloromethyl methyl ether (6.0 mL) was added. After stirring at 40° C. for 18 hours, methanol (20 mL) was added at room temperature. After stirring for 1.5 hours, potassium carbonate (11 g, 39.7 mmol) was added, followed by stirring overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 10.87 g of the title compound (yield: 79%) as a pale yellow oil.

Workup

stirringAfter stirring for 1.5 hours
stirringby stirring overnight
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-06c26e4c109a4f029ca12235b88747f9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168666B2

Reaction notes

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