Potassium Carbonate → Phenol, 2,6-bis(1,1-dimethylethyl)-4-[[(dimethylphenylsilyl)methyl]thio]-

HRID 1737187Notes

Reaction equation

HRID 1737187 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([SH: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(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][Si:25]([CH3:33])([CH3:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[C:12]([C:7]1[CH:8]=[C:9]([S:11][CH2:24][Si:25]([CH3:33])([CH3:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:16])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 74598(Chloromethyl)dimethylphenylsilane

Product 1

HCID 11485998Phenol, 2,6-bis(1,1-dimethylethyl)-4-[[(dimethylphenylsilyl)methyl]thio]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix 2,6-di-t-butyl-4-mercaptophenol (2.4 g, 10 mmol), potassium carbonate (1.4 g, 10 mmol), chloromethyldimethylphenylsilane (1.9 g, 10 mmol) and dimethylformamide (50 mL) and stir overnight at room temperature under argon atmosphere. Dilute the mixture with ice-water and extract with ethyl ether. Wash the ethereal layer with water, then brine, filter through flourosil-Na2SO4, and evaporate to an orange oil (3.5 g). Purify the product by first distilling (bp 160-170° C. @ 0.1 mm Hg), then subjecting to silica gel chromatography (CCl4 :CHCl3 /1:1) to obtain the title compound as a light yellow oil which slowly crystallizes to a white waxy solid (2.3 g, 59%). Anal. Calcd for C23H34OSSi: C, 71.44; H, 8.86; S, 8.29; Found: C, 71.14; H, 8.86; S, 7.98.

Workup

  1. extractionextract with ethyl ether
  2. washWash the ethereal layer with water
  3. filtrationbrine, filter through flourosil-Na2SO4
  4. customevaporate to an orange oil (3.5 g)
  5. customPurify the product
  6. distillationby first distilling (bp 160-170° C. @ 0.1 mm Hg)

Sources & evidence

ORD record
ord-e8b14475cb27411b9d01d6f221d5c53f
Source dataset
uspto-grants-1999_10
Patent number
US05962435

Reaction notes

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