p-Chlorothiophenol → HCID 13937441, compound

HRID 653064Notes

Reaction equation

HRID 653064 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH3:15]>O>[CH2:11]([S:10][C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 80571-BromopentaneHCID 14798Sodium Hydroxide

Product 1

HCID 13937441HCID 13937441, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 8.0 g (0.2 mole) of sodium hydroxide in 100 ml of water is added 29 g (0.2 mole) of p-chlorothiophenol in small portions. Stirring is continued until the mixture becomes clear. To this solution is added 30.2 g (0.2 mole) of pentyl bromide dropwise. The reaction mixture is heated at 60° C. for one hour. It is then poured into water and extracted with ether. The combined ether extracts are washed with water and dried over MgSO4. Solvent is evaporated to give a pale yellow oil which is purified further by vacuum distillation (85°-8°/0.03 mm) to give 15 g of pure product.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed with water
  3. dry with materialdried over MgSO4
  4. customSolvent is evaporated
  5. customto give a pale yellow oil which
  6. distillationis purified further by vacuum distillation (85°-8°/0.03 mm)

Sources & evidence

ORD record
ord-f6a32c216e7243f9beada63d2d4dddbf
Source dataset
uspto-grants-1987_06
Patent number
US04675316

Reaction notes

Loading…