Toluene → Benzene, [(pentyloxy)methyl]-
Reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OOC(C)(C)C)(C)(C)C>>[C:7]1([CH2:13][O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
4
Conditions
- Temperature
- 90 °C
Procedure
Into a pressure vessel 1-pentanol (109 μL, 1 mmol, 1 eq) was added and diluted with toluene (1.063 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 toluene under vacuum, the residue was analyzed by 1H NMR and GC/MS to determine the yield and consumption of starting materials. 1H NMR Yield: 20%.
Workup
- customthe pressure vessel was sealed
- customThe catalyst was separated
- filtrationfiltering through Celite®
- customAfter removing toluene under vacuum
- customyield
- customconsumption of starting materials
Sources & evidence
- ORD record
- ord-5d749d07aa6f4c2a9234c1af74e1af5c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416080B2
Reaction notes
Loading…