Methane, dichloromethoxy- → 6-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde

HRID 2404199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404199
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.[CH3:28][O:29]C(Cl)Cl>ClCCCl.ClCCl>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([O:11][C:12]2[CH:21]=[C:20]3[C:15](=[C:14]([CH3:22])[CH:13]=2)[CH:16]=[C:17]([CH:28]=[O:29])[CH:18]=[CH:19]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 681727973-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene

Produkt 1

HCID 866684296-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehydeAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 3-(4-tert-butyl-cyclohexyloxy)-1-methyl-naphthalene (450 mg, 1.5 mmol) in 1,2-dichloroethane (9 mL) was added tin tetrachloride (236 uL, 2 mmol) at 0° C. After stirred at 0° C. for 1 hr, dichloromethyl methyl ether (183 uL, 2 mmol) was added. The solution was stirred at 0° C. for 1 hr and then warmed to room temperature. The mixture was added ice water and stirred for 1 hr, then the dark solution was diluted with dichloromethane and washed with water. The organic phase was washed with sodium bicarbonate aqueous, and dried over MgSO4. The drying agent was filtered off and the solvent was concentrated to dryness to give dark solid product (0.48 g, yield: 97%). ESI-MS: 325.20 (M+H)+.

Aufarbeitung

  1. stirringThe solution was stirred at 0° C. for 1 hr
  2. temperaturewarmed to room temperature
  3. stirringstirred for 1 hr
  4. washwashed with water
  5. washThe organic phase was washed with sodium bicarbonate aqueous
  6. dry with materialdried over MgSO4
  7. filtrationThe drying agent was filtered off
  8. concentrationthe solvent was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c4eff4b594a346c0a18c8160f707311f
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

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