Heptanol → 1-Heptoxy-3,5-dimethylbenzene

HRID 1243064Notes

Reaction equation

HRID 1243064 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.CC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C([O-])([O-])=O.[Cs+].[Cs+].CCCCCCCCCCCC>[Cu]I.C1(C)C=CC=CC=1>[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 8129HeptanolHCID 8182DodecaneHCID 10796Cesium carbonateHCID 727915-Methyl-1,10-phenanthrolineHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 155310051-Heptoxy-3,5-dimethylbenzeneYield 68%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A screw cap test tube was charged with ii-heptanol (283 μl, 2.00 mmol), 3,5-dimethyliodobenzene (144 μL, 1.00 mmol), CuI (19.0 mg, 0.100 mmol), 5-methyl-1,10-phenanthroline (38.8 mg, 0.200 mmol), Cs2CO3 (977 mg, 3.00 mmol) and toluene (0.5 mL). The test tube was sealed with a screw cap. The reaction mixture was stirred magnetically and heated at 70° C. for 23 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 68% 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-c41d88c1bc984709b8bb73a69ab18722
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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