Methanol → (1-Methoxyethyl)benzene

HRID 1482757Notes

Reaction equation

HRID 1482757 reaction equation
CO.[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:4].[C:11]([O:15]OC(C)(C)C)(C)(C)C>>[C:5]1([CH:3]([CH3:4])[O:15][CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Conditions

Temperature
90 °C

Procedure

Into a pressure vessel methanol (84 μL, 1 mmol, 1 eq) was added and diluted with ethylbenzene (1.225 mL, 10 mmol, 10 eq). To this stirring solution was added 1 mol % of a stock solution of {[Cl2NN]Cu}2(benzene) from the catalyst stock solution described in Example 4 (200 μL=0.01 mmol). After adding of tert-butyl peroxide (220 μL, 1.2 mmol), the pressure vessel was sealed and heated to 90° C. for 24 hr. The catalyst was separated by exposing the mixture to air and filtering through Celite®. After removing ethylbenzene under vacuum, the residue was analyzed by GC/MS and 1H NMR to determine the yield and consumption of starting materials. 1H NMR Yield: 35%.

Workup

  1. customthe pressure vessel was sealed
  2. customThe catalyst was separated
  3. filtrationfiltering through Celite®
  4. customAfter removing ethylbenzene under vacuum
  5. customyield
  6. customconsumption of starting materials

Sources & evidence

ORD record
ord-ef33535f270348ecb34c7c17495ca65c
Source dataset
uspto-grants-2016_08
Patent number
US09416080B2

Reaction notes

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