Water → 3-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene

HRID 2404198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404198
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.[C:13]([CH:17]1[CH2:22][CH2:21][CH:20](OS(C)(=O)=O)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(O)(C)C.CC(=O)CC.CCOCC>[C:13]([CH:17]1[CH2:22][CH2:21][CH:20]([O:12][C:4]2[CH:3]=[C:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11128255Methanesulfonic acid 4-tert-butyl-cyclohexyl esterHCID 125809284-Methylnaphthalen-2-ol

Produkt 1

HCID 681727973-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthaleneAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-methyl-naphthalen-2-ol (0.60 g, 3.8 mmol), methanesulfonic acid 4-tert-butyl-cyclohexyl ester (1.9 g, 7.6 mmol) and cesium carbonate (3.7 g, 11 mmol) in t-BuOH (10 mL) and 2-butanone (7 mL) was heated at 80° C. overnight. After cooled to room temperature, the mixture was treated with water and ether. The organic phase was dried over MgSO4, filtered and concentrated. The crude was treated with methanol to give solid product (0.55 g, yield: 48%). ESI-MS: 297.20 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude was treated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-282cd8774d5a43658a784d9384a51f01
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

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