Acetic Acid → 1,1,1,3,3,3-Hexafluoro-2-[2-(hydroxymethyl)-4-(methoxymethoxy)-3-propylphenyl]propan-2-ol
Reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[C:11]([CH2:19][CH2:20][CH3:21])[C:10]=1[CH2:22][O:23]C1CCCCO1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1.O>[F:1][C:2]([F:30])([F:31])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[C:11]([CH2:19][CH2:20][CH3:21])[C:10]=1[CH2:22][OH:23])([OH:8])[C:4]([F:5])([F:7])[F:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1,1,1,3,3,3-hexafluoro-2-[4-(methoxymethoxy)-3-propyl-2-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl]propan-2-ol (883.2 mg, 1.92 mmol) in tetrahydrofuran (10 mL), water (5 mL), and acetic acid (20 mL) were added, and the mixture was stirred at 50° C. for 3 hours. The reaction solution was neutralized with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate. The organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated under vacuum. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (678 mg, 92%) was obtained as colorless oil.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated saline
- customdried
- concentrationconcentrated under vacuum
- customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-d2d72ce664f44eb29d43defccca5ebbb
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951822B2
Reaction notes
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