1,10-Phenanthroline → 1-Heptoxy-3,5-dimethylbenzene

HRID 1883411Notes

Reaction equation

HRID 1883411 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:9][C:10]1[CH:11]=[C:12](I)[CH:13]=[C:14]([CH3:16])[CH:15]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].CCCCCCCCCCCC>[Cu]I.CC1C=CC=CC=1C>[CH2:1]([O:8][C:12]1[CH:13]=[C:14]([CH3:16])[CH:15]=[C:10]([CH3:9])[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 5

HCID 13181,10-PhenanthrolineHCID 8129HeptanolHCID 8182DodecaneHCID 10796Cesium carbonateHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 155310051-Heptoxy-3,5-dimethylbenzeneYield 64%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A screw cap test tube was charged with n-heptanol (283 μL, 2.00 mmol), 3,5-dimethyliodobenzene (144 μL, 1.00 mmol), CuI (4.75 mg, 0.025 mmol), 1,10-phenanthroline (1.80 mg, 0.01 mmol), Cs2CO3 (977 mg, 3.00 mmol) and o-xylene (1 mL). The test tube was sealed with a screw cap. The reaction mixture was stirred magnetically and heated at 120° C. for 19 hours. The reaction mixture was allowed to reach room temperature. Dodecane (227 μL, 1.00 mmol; internal standard) was added and a GC sample was filtered through Celite and eluted with CH2Cl2. GC analysis revealed 64% yield of the desired product.

Workup

  1. customA screw cap test tube
  2. customThe test tube was sealed with a screw
  3. customcap
  4. customto reach room temperature
  5. filtrationa GC sample was filtered through Celite
  6. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-46ee2b3e25b94ca0aa71c8c47c30ca85
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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