4-(Benzyloxy)-3-(trifluoromethyl)benzoic acid → (4-Benzyloxy-3-trifluoromethylphenyl)methanol

HRID 19939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19939
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[C:18]([F:19])([F:21])[F:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 167490234-(Benzyloxy)-3-(trifluoromethyl)benzoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 16749447(4-Benzyloxy-3-trifluoromethylphenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

4-Benzyloxy-3-trifluoromethyl-benzoic acid (CAB03046, 3.555 g, 12 mmol) in THF (20 mL) was added dropwise to a suspension of lithium aluminum hydride (1.0 g, 26.3 mmol) in THF (20 mL). The mixture was stirred for another 30 minutes at room temperature and then quenched by addition of 2N NaOH (5 mL). The white precipitate was filtered off and washed with dichloromethane (100 mL), the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The resulting oil was crystallised from diethyl ether/hexane. Yield: 3.31 g (98%). 1H-NMR (400 MHz, CDCl3)=1.72 (t, J=5.9 Hz, 1H, —OH), 4.66 (d, J=5.9 Hz, 2H, —CH2OH), 5.21 (s, 2H, —CH2Ph), 7.02 (d, J=8.2 Hz, 1H), 7.30-7.48 (m, 6H), 7.61 (d, J=2.3 Hz, 1H). LRMS (FAB+): 91.1 (100), 265.2 (45), 282.2 (40, [M+H]+.

Aufarbeitung

  1. customquenched by addition of 2N NaOH (5 mL)
  2. filtrationThe white precipitate was filtered off
  3. washwashed with dichloromethane (100 mL)
  4. dry with materialthe filtrate was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil was crystallised from diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c13885aa43784e799265b8210021ee3e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745472B2

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