Carbon Dioxide → 7-(4-Methoxyphenyl)heptyl phenyl sulfide

HRID 426877Notes

Reaction equation

HRID 426877 reaction equation
C1([Li])C=CC=CC=1.[C:8]1([S:14][CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]I)=[CH:23][CH:22]=1>O.O1CCCC1>[C:8]1([S:14][CH2:15][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:24]2[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7520ThioanisoleHCID 14977896HCID 14977896, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 203899877-(4-Methoxyphenyl)heptyl phenyl sulfide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Phenyllithium (378 ml., 0.755 mole) was added over a period of 2-5 minutes to a solution of 94.5 g. of thioanisole in 600 ml. of tetrahydrofuran, stirred under nitrogen. The mixture was stirred at room temperature for about 16 hours, then cooled to -70° C. (solid CO2), and 141 g. of 6-(4-methoxyphenyl)hexyl iodide in 210 ml. of tetrahydrofuran was added slowly. The reaction mixture was stirred at -65° C. for two hours and then allowed to warm to room temperature. Water was added and the mixture extracted with pentane. The pentane extracts were washed with water, dried and concentrated to remove the solvent. The residue was distilled in vacuo, b.p. 171°-174° C. (0.15 mm.). The distillate crystallized and was recrystallized from pentane, to give 7-(4-methoxyphenyl)heptyl phenyl sulfide, m.p. 58°-59° C.

Workup

  1. stirringThe reaction mixture was stirred at -65° C. for two hours
  2. temperatureto warm to room temperature
  3. extractionthe mixture extracted with pentane
  4. washThe pentane extracts were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto remove the solvent
  8. distillationThe residue was distilled in vacuo, b.p. 171°-174° C. (0.15 mm.)
  9. customThe distillate crystallized
  10. customwas recrystallized from pentane

Sources & evidence

ORD record
ord-04c5aa86b45945959167d1b9faf4261f
Source dataset
uspto-grants-1979_10
Patent number
US04171378

Reaction notes

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