Ethylene Glycol → HCID 11148597, compound

HRID 2253506Notes

Reaction equation

HRID 2253506 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(O)CO.I[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCCCCCCCCCCC>[Cu-]=O.C(OCC)(=O)C.CC(O)C>[CH3:18][C:16]1[CH:17]=[C:12]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[C:14]([CH3:19])[CH:15]=1

Participants

9

Reactant 5

HCID 174Ethylene GlycolHCID 7969ThiophenolHCID 8182DodecaneHCID 11430Potassium CarbonateHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 11148597HCID 11148597, compound

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Copper(I) oxide (7.2 mg, 0.05 mmol) and potassium carbonate (276 mg, 2.0 mmol) were added to a screw-capped test tube with a Teflon-lined septum. The tube was evacuated and backfilled with argon (3 cycles). 2-Propanol (1.0 mL, bench top grade solvent without degassing and pre-drying), ethylene glycol (111 μL, 2.0 mmol, bench top grade solvent) and 5-iodo-m-xylene (144 μL, 1.0 mmol) and thiophenol (103 μL, 1.0 mmol) were added by syringes at room temperature. The tube was heated to 80° C. and stirred for 20 hours. The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 μL, GC standard) were added. The aliquot was analyzed by GC to give 93% conversion of ArI and 93% GC yield of phenyl 3,5-dimethylphenyl sulfide.

Workup

  1. customThe tube was evacuated
  2. customto reach room temperature

Sources & evidence

ORD record
ord-5e58e13c45674ad8974d8a2d5e274393
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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