Hydrochloric Acid → 4-Methyl-alpha-(trifluoromethyl)benzenemethanol

HRID 469843

Reaktionsgleichung

Reaktionsgleichung von HRID 469843
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.[Si]([C:32]([F:35])([F:34])[F:33])(C)(C)C.Cl>C1COCC1>[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]([OH:25])[C:32]([F:35])([F:34])[F:33])=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 77254-MethylbenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Produkt 1

HCID 3472044-Methyl-alpha-(trifluoromethyl)benzenemethanolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (0.1 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 4-methyl-benzaldehyde (1.2 g, 10 mmol) and TMSCF3 (1.8 ml, 12 mmol) in 10 ml THF at 0° C. The formed mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was then treated with 12 ml of 1N HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 1.6 g of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol, yield 86%.

Aufarbeitung

  1. stirringstirred overnight
  2. extractionThe product was extracted with ethyl acetate (3×20 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f772296702584698a376c0c22b223996
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629156B2

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