1-Pentanol → HCID 53729181, compound

HRID 1482753Notes

Reaction equation

HRID 1482753 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8].C(OOC(C)(C)C)(C)(C)C>>[C:9]1([CH:7]([CH3:8])[O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 62761-PentanolHCID 7500EthylbenzeneHCID 8033Di-tert-butyl peroxide

Product 1

HCID 53729181HCID 53729181, compoundYield 48%

Conditions

Temperature
90 °C

Procedure

Into a pressure vessel 1-pentanol (109 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 ethyl benzene under vacuum, the residue was analyzed by GC/MS and 1H NMR to determine the yield and consumption of starting materials. 1H NMR Yield: 48%.

Workup

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

Sources & evidence

ORD record
ord-254341dee2604059b8531ef7f92fc11c
Source dataset
uspto-grants-2016_08
Patent number
US09416080B2

Reaction notes

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