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Acetic Acid → 1,1,1,3,3,3-Hexafluoro-2-[2-(hydroxymethyl)-4-(methoxymethoxy)-3-propylphenyl]propan-2-ol

HRID 552449
Notes
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Reaction equation

HRID 552449 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 579008411,1,1,3,3,3-hexafluoro-2-[4-(methoxymethoxy)-3-propyl-2-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl]propan-2-ol

Product 1

HCID 579007901,1,1,3,3,3-Hexafluoro-2-[2-(hydroxymethyl)-4-(methoxymethoxy)-3-propylphenyl]propan-2-olYield 93.8%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated under vacuum
  5. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951822B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes