1-Butanol → HCID 12945988, compound

HRID 1883402Notes

Reaction equation

HRID 1883402 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH:8]=[C:9](I)[CH:10]=[C:11]([CH3:13])[CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(C2C=CC=CC=2O)C=CC=CC=1.CCCCCCCCCCCC>[Cu]I>[CH2:1]([O:5][C:9]1[CH:10]=[C:11]([CH3:13])[CH:12]=[C:7]([CH3:6])[CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 2631-ButanolHCID 7017(1,1'-Biphenyl)-2-olHCID 8182DodecaneHCID 10796Cesium carbonateHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 12945988HCID 12945988, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
90 °C

Procedure

A screw cap test tube was charged with n-butanol (573 μL, 6.26 mmol), 3,5-dimethyliodobenzene (144 μL, 1.00 mmol), CuI (19.0 mg, 0.100 mmol), Cs2CO3 (977 mg, 3.00 mmol), 2-phenylphenol (85.1 mg, 0.500 mmol) and the solvent (1 mL). The test tube was sealed with a screw cap. The reaction mixture was stirred magnetically and heated at 90° C. for 36 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. The yield of the desired product was determined using GC analysis; the results are tabulated below.

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-65f1778bc5a64ed8b6ae6a467a599ac9
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

Loading…