Chlorotrimethylsilane → HCID 18406232, compound

HRID 1016223Notes

Reaction equation

HRID 1016223 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH:11]([OH:20])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[CH3:26][Si:27]([CH3:30])([CH3:29])Cl.Cl[SiH3]>C1(C)C=CC=CC=1>[C:21]([C:7]1[CH:8]=[C:9]([CH:11]([O:20][Si:27]([CH3:30])([CH3:29])[CH3:26])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:25])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 61622ChlorosilaneHCID 18406237HCID 18406237, compound

Product 1

HCID 18406232HCID 18406232, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a nitrogen-purged 250 mL three-neck round-bottom flask were added 141 grams (0.41 mole) of the 2,6-di-t-butyl-4-(1-hydroxy-3-phenylpropyl)phenol produced in step (A) of this example, 100 mL of toluene, and 54.3 grams (0.50 mole) of trimethylchlorosilane. The addition of the chlorosilane produced a several degree exotherm. The mixture was allowed to stir overnight at ambient temperature. After this time, the reaction mixture was washed with water (3×200 mL), dried with sodium sulfate, and filtered. Removal of the hexane gave 148.9 grams of desired product (87.1 percent).

Workup

  1. customTo a nitrogen-purged 250 mL three-neck round-bottom flask
  2. customproduced a several degree exotherm
  3. washAfter this time, the reaction mixture was washed with water (3×200 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customRemoval of the hexane

Sources & evidence

ORD record
ord-ca3e11398ee44f61ae3a33c6d8e1afb9
Source dataset
uspto-grants-2002_11
Patent number
US06475347B1

Reaction notes

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