Acetonitrile → Chloro(2,6-di-tert-butyl-4-methylphenoxy)dimethylsilane

HRID 1981631Notes

Reaction equation

HRID 1981631 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].C(#N)C.[Cl:20][Si:21](Cl)([CH3:23])[CH3:22]>C(N(CC)CC)C>[C:12]([C:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[O:16][Si:21]([CH3:23])([CH3:22])[Cl:20])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6398DichlorodimethylsilaneHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 13254327Chloro(2,6-di-tert-butyl-4-methylphenoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2,6-di-t-butyl-4-methylphenol (110 g, 0.5M), acetonitrile (500 ml), triethylamine (70 ml, 0.5M) and dichlorodimethylsilane (61 ml, 0.5M) was refluxed for 16 hours. The solvent was evaporated and the residue extracted with toluene (500 ml). The toluene extract was evaporated and the residue recrystallised from acetonitrile to give the title compound (90 g, 57%) m.p. 119°-121° (Found: C, 65 65; H, 9.4%. C17H29ClOSi requires C, 65.2; H, 9.3%).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe solvent was evaporated
  3. extractionthe residue extracted with toluene (500 ml)
  4. extractionThe toluene extract
  5. customwas evaporated
  6. customthe residue recrystallised from acetonitrile

Sources & evidence

ORD record
ord-853425ba1c3f4d0ca292082c232984aa
Source dataset
uspto-grants-1986_06
Patent number
US04593111

Reaction notes

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