Sulfuric Acid → HCID 14650104, compound

HRID 1073413Notes

Reaction equation

HRID 1073413 reaction equation
[H-].[Na+].C(S)C.[CH3:6][CH:7]([S:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=1)[CH2:8][CH3:9].S(=O)(=O)(O)O>CN(C=O)C>[CH3:6][CH:7]([S:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 14852816HCID 14852816, compound

Product 1

HCID 14650104HCID 14650104, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To sodium hydride (6.6 g, 275.0 mmol; prewashed with pentane) in 100 ml of DMF, under N2 and at 5°, is slowly added ethyl mercaptan (41.0 ml, 550.0 mmol) in 50 ml of DMF. This mixture is stirred for 1.5 hours, after which is added 4-(1methylpropylthio)anisole (46.0 g, 250.0 mmol) and DMF. The mixture is heated to 150° with stirring overnight. After cooling to 20°, 10% aqueous sulfuric acid is added and the mixture is extracted with ether. The combined organic layers are washed with water and extracted with 5% NaOH. The aqueous portion is reacidified with conc. sulfuric acid and extracted with ether. The combined ether extracts are washed with water and with brine, dried and the solvent removed to give 4-(1methylpropylthio)phenol.

Workup

  1. customat 5°
  2. temperatureThe mixture is heated to 150°
  3. stirringwith stirring overnight
  4. temperatureAfter cooling to 20°
  5. extractionthe mixture is extracted with ether
  6. washThe combined organic layers are washed with water
  7. extractionextracted with 5% NaOH
  8. extractionextracted with ether
  9. washThe combined ether extracts are washed with water and with brine
  10. customdried
  11. customthe solvent removed

Sources & evidence

ORD record
ord-5aca4e169ba74a4abd8c8f79189562f0
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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