Water → (4-Cyclohexylphenyl)methanol

HRID 530533

Reaktionsgleichung

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[K+]>CCOCC>[CH:7]1([C:13]2[CH:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:20][CH:21]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (2.0 M THF solution, 5.3 mL, 10.53 mmol) in dry Et2O (10 mL), commercially available 4-cyclohexylbenzoic acid (0.5 g, 2.45 mmol) in dry Et2O (5.0 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.45 mL), 3.0 M KOH solution (0.45 mL) and H2O (2.0 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.46 g, quant.), which was used in the next step without any further purification. 1H NMR (CDCl3): δ 8.05-7.94 (m, 2H), 7.35-7.23 (m, 2H), 4.39 (q, 2H, J=7.12 Hz), 2.59 (tt, 1H J=11.41, 3.27 Hz), 1.97-1.73 (m, 5H), 1.53-1.34 (m, 6H).

Aufarbeitung

additionwas added dropwise
waitThe mixture was left
customto react at rt for 4 h
customat 0° C
filtrationfiltered
customto remove the solid residue
dry with materialthe organic phase dried over Na2SO4
filtrationThe organic solution was again filtered
concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-2467069b133d450c8711dba189212175
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09353075B2

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