Hydrochloric Acid → 2,6-Di-tert-butyl-4-({[dodecyl(dimethyl)silyl]methyl}sulfanyl)phenol

HRID 1737188Notes

Reaction equation

HRID 1737188 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]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH3:27])[CH3:26].Cl>CN(C)C=O>[C:12]([C:7]1[CH:8]=[C:9]([S:11][CH2:24][Si:25]([CH3:26])([CH3:27])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:16])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 116904Silane, (chloromethyl)dodecyldimethyl-

Product 1

HCID 158723352,6-Di-tert-butyl-4-({[dodecyl(dimethyl)silyl]methyl}sulfanyl)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix 2,6-di-t-butyl-4-mercaptophenol (2.4 g, 10 mmol), potassium carbonate (1.7 g, 12.3 mmol), chloromethyldodecyldimethylsilane (2.8 g, 10 mmole) and dimethylformamide (50 mL) and stir overnight at room temperature under argon atmosphere. Dilute the mixture with ice-water, acidify with aqueous hydrochloric acid and extract with ethyl ether. Wash the ethereal layer with water, then brine, filter through fluorosil-Na2SO4 and evaporate to an orange semi-solid (4.0 g). Purify the product by first distilling (180-200° C. @ 0.1 mm Hg) then subjecting to silica gel chromatography (CCl4) to obtain the title compound as a colorless oil which slowly crystallizes.

Workup

  1. extractionextract with ethyl ether
  2. washWash the ethereal layer with water
  3. filtrationbrine, filter through fluorosil-Na2SO4
  4. customevaporate to an orange semi-solid (4.0 g)
  5. customPurify the product
  6. distillationby first distilling (180-200° C. @ 0.1 mm Hg)

Sources & evidence

ORD record
ord-80d37c79c8b44fc68459f0b41ea1cb74
Source dataset
uspto-grants-1999_10
Patent number
US05962435

Reaction notes

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