Water → HCID 121388233, compound

HRID 2204773Notes

Reaction equation

HRID 2204773 reaction equation
[S:1]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[C:16]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:15]=1)[C:2]1[C:7]([CH3:8])=[CH:6][C:5](O)=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[C:26](=[O:29])([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].O>CN(C)C=O>[C:10]([C:4]1[C:5]([O:29][CH2:26][CH2:7][CH2:2][CH2:3][CH3:4])=[CH:6][C:7]([CH3:8])=[C:2]([S:1][C:14]2[CH:15]=[C:16]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]([O:21][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:18][C:19]=2[CH3:20])[CH:3]=1)([CH3:11])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7308SantonoxHCID 80571-BromopentaneHCID 11430Potassium Carbonate

Product 1

HCID 121388233HCID 121388233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,4′-thiobis(2-(tert-butyl)-5-methylphenol) (4,4′-thiobis(6-tert-butyl-m-cresol)) (1 equivalent (eq), 10 g, 27.89 mmol), potassium carbonate (2.5 eq, 9.6363 g, 69.725 mmol, 138.205 g/mol), and 1-bromopentane (2.1 eq, 8.8463 g, 7.3 mL, 58.569 mmol, 151.04 g/mol, d=1.218 g/mL) were dissolved in N,N-dimethylformamide (DMF, 90 mL) at 90° C. The reaction was stirred until complete as determined by thin layer chromatography (TLC). The reaction was poured into water and extracted with ethyl acetate. The aqueous layer was discarded and the ethyl acetate was back-extracted three times with brine to remove residual DMF. The resulting organic solution was dried with magnesium sulfate, filtered, and concentrated on a rotary evaporator. The crude product was recrystallized from methanol, filtered, and then washed with cold methanol. The product was dried at 50° C. under high vacuum for 12 hours to yield a fine white powder (compound characterized by Structure F: bis(5-(tert-butyl)-2-methyl-4-(pentyloxy)phenyl)sulfane). The yield was 8.4211 g (60.5%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe ethyl acetate was back-extracted three times with brine
  3. customto remove residual DMF
  4. dry with materialThe resulting organic solution was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customThe crude product was recrystallized from methanol
  8. filtrationfiltered
  9. washwashed with cold methanol
  10. customThe product was dried at 50° C. under high vacuum for 12 hours

Sources & evidence

ORD record
ord-825a3157a6eb4aaa9ad87e8d386c0405
Source dataset
uspto-grants-2016_06
Patent number
US09366661B1

Reaction notes

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