Hydrochloric Acid → 4-(1,2,2,6,6-Pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol

HRID 237745

Reaktionsgleichung

[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=O)[CH2:4][C:3]1([CH3:12])[CH3:11].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[OH-].[NH4+]>>[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH:6]=[C:5]([C:16]2[CH:17]=[CH:18][C:13]([OH:19])=[CH:14][CH:15]=2)[CH2:4][C:3]1([CH3:12])[CH3:11]

Komponenten

Edukt 4

HCID 313Hydrochloric Acid

HCID 996Phenol

HCID 14923Ammonium Hydroxide

HCID 2419551,2,2,6,6-Pentamethyl-4-piperidone

Produkt 1

HCID 685241834-(1,2,2,6,6-Pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenolAusbeute 34 %

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

1,2,2,6,6-Pentamethyl-piperidin-4-one (8.64 g, 50.00 mmol) and phenol (4.98 g, 53.00 mmol) were melted together at 60° C. in a 100 mL round bottomed flask after which 13.5 mL of concentrated hydrochloric acid was added dropwise. The yellow solution was stirred at 70° C. for 24 hours. The mixture was poured into a beaker containing ice. Ammonium hydroxide was added carefully while stirring until the pH reached 7˜8. The mixture was extracted with EtOAc five times. The organic phases were combined, dried (Na2SO4) and concentrated. The residue was purified by chromatography on a silica gel column, eluting with 7N NH3 in methanol/dichloromethane to give 4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol (4.11 g, 34%).

Aufarbeitung

additionThe mixture was poured into a beaker
additioncontaining ice
stirringwhile stirring until the pH
extractionThe mixture was extracted with EtOAc five times
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified by chromatography on a silica gel column
washeluting with 7N NH3 in methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-f69f7ec3095f4145ab52f743f9a5268d
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642603B2

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