3,7-Dimethyloctyl trichlorosilane → 3,7-Dimethyloctyl-n-hexyl-dichlorosilane

HRID 1504242Notes

Reaction equation

HRID 1504242 reaction equation
[CH3:1][CH:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][CH2:4][Si:5]([Cl:8])([Cl:7])Cl.[CH2:15]([Mg]Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH3:1][CH:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[CH2:3][CH2:4][Si:5]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([Cl:7])[Cl:8]

Participants

4

Reactant 2

HCID 1240151143,7-Dimethyloctyl trichlorosilaneHCID 178444609HCID 178444609, compound

Product 1

HCID 1232579153,7-Dimethyloctyl-n-hexyl-dichlorosilaneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (50 ml) and 3,7-dimethyloctyl trichlorosilane (11.0 g, 40.0 mmol) were placed in a 200 mL four-necked flask in a nitrogen atmosphere, and cooled to −20° C. n-hexyl magnesium bromide (Sigma-Aldrich Co. LLC., 2.0 M, 21 ml) was added dropwise, and the mixture was agitated for 1 hour at 10° C. or less. The temperature was raised gradually to room temperature over the course of about 1 hour, and the mixture was left standing overnight. The precipitated salt was filtered out, the tetrahydrofuran was removed by concentration under reduced pressure, and the mixture was distilled under reduced pressure to obtain the target 3,7-dimethyloctyl-n-hexyl-dichlorosilane (Compound E24) (127-130° C./0.26 Torr, 9.5 g, yield 73%).

Workup

  1. additionwas added dropwise
  2. waitthe mixture was left
  3. waitstanding overnight
  4. filtrationThe precipitated salt was filtered out
  5. customthe tetrahydrofuran was removed by concentration under reduced pressure
  6. distillationthe mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-fc1baade5a634cd1915b27c257726f66
Source dataset
uspto-grants-2015_12
Patent number
US09212254B2

Reaction notes

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