Water → HCID 121388231, compound

HRID 2204774Notes

Reaction equation

HRID 2204774 reaction equation
[S:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O>CN(C=O)C>[CH2:23]([O:15][C:12]1[CH:13]=[CH:14][C:9]([S:1][C:2]2[CH:7]=[CH:6][C:5]([O:19][CH2:16][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 175704,4'-Thiodiphenol

Product 1

HCID 121388231HCID 121388231, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,4′-thiodiphenol (bis(4-hydroxyphenyl) sulfide) (1 eq, 10 g, 45.8 mmol), potassium carbonate (2.5 eq, 15.8245 g, 114.5 mmol, 138.205 g/mol), and 1-bromoheptane (2.5 eq, 20.5070 g, 18 mL, 114.5 mmol, 179.10 g/mol, d=1.14 g/mL) were dissolved in DMF (100 mL) at 80° C. The reaction was stirred until complete as determined by TLC. The reaction was poured into water and extracted with dichloromethane (DCM). The aqueous layer was discarded and the DCM was back-extracted three times to remove residual DMF. The resulting organic solution was dried with sodium sulfate, filtered, and concentrated on a rotary evaporator. The product was recrystallized from ethanol, filtered, and then washed with cold ethanol. The product was subsequently put through a silica plug with 50-50 hexanes-DCM and concentrated on a rotary evaporator to yield a white powder (compound characterized by Structure B: bis(4-(heptyloxy)phenyl)sulfane). The product was dried under high vacuum for 24 hours at 50° C. to remove residual solvents and 1-bromoheptane. The yield was 5 g (26.3%)

Workup

  1. extractionextracted with dichloromethane (DCM)
  2. extractionthe DCM was back-extracted three times
  3. customto remove residual DMF
  4. dry with materialThe resulting organic solution was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customThe product was recrystallized from ethanol
  8. filtrationfiltered
  9. washwashed with cold ethanol
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-b26bbb9635fa496d9a3da59b062112b9
Source dataset
uspto-grants-2016_06
Patent number
US09366661B1

Reaction notes

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