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Formaldehyde → 2-(Hydroxymethyl)-4-(trifluoromethyl)phenol

HRID 392912
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 392912
C=O.[F:3][C:4]([F:13])([F:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C1(B(O)O)C=CC=CC=1.[C:23](O)(=[O:26])CC.OO>C1C=CC=CC=1.C1COCC1.O>[OH:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([F:12])([F:13])[F:3])=[CH:10][C:9]=1[CH2:23][OH:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 712FormaldehydeHCID 784Hydrogen PeroxideHCID 1032Propionic AcidHCID 66827Phenylboronic AcidHCID 678744-(Trifluoromethyl)phenol

Produkt 1

HCID 233631292-(Hydroxymethyl)-4-(trifluoromethyl)phenolAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Paraformaldehyde (3.4 g, 0.114 mol) was added in 0.5 g portions over a six hour period to a refluxing mixture of 4-trifluoromethyl phenol (2.3 g, 0.0142 mol), phenyl boronic acid (2.1 g, 0.017 mol) and proprionic acid (530 μL, 7 mmol) in benzene with the azeotropic removal of water (Dean-Stark trap). When the addition was complete, the reaction was heated for an additional hour, then cooled with an ice bath, diluted with THF (30 mL) and treated with 5 mL of 30% hydrogen peroxide solution. After stirring for one hour, the mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with NaHSO3 solution (1×50 mL), brine (1×50 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (30% ethyl acetate/hexanes) to afford 950 mg (35%) of the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.42 (d, 1H, J=9.1 Hz); 7.3 (s, 1H); 6.95 (d, 1H, J=9.1 Hz); 4.89 (s, 2H);

Aufarbeitung

  1. additionWhen the addition
  2. temperaturethe reaction was heated for an additional hour
  3. temperaturecooled with an ice bath
  4. customthe mixture was partitioned between water (50 mL) and ethyl acetate (50 mL)
  5. washThe organic layer was washed with NaHSO3 solution (1×50 mL), brine (1×50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-81500cb4265c40f2b2387409994cb0c0
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06803457B1

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