p-Chlorothiophenol → 4-(p-Chlorophenylthio)butyl acetate

HRID 1703545

Reaction equation

HRID 1703545 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]Cl)(=[O:11])[CH3:10].[OH-].[Na+]>C(O)C>[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][S:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 14798Sodium HydroxideHCID 233991-Butanol, 4-chloro-, 1-acetate

Product 1

HCID 227621174-(p-Chlorophenylthio)butyl acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 144.6 g of p-chlorothiophenol, 150.6 g of 4-chlorobutyl acetate, 80 g of 50% aqueous solution of sodium hydroxide and 750 ml of ethyl alcohol was heated under reflux for 5 hours. The alcohol was distilled off and ether was added to the cool mixture. After washing with dilute sodium hydroxide solution and then water, the ether solution was dried, evaporated to dryness and distilled. The product was collected at 110°-116° and 0.01 mm, ND25 1.5480.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. distillationThe alcohol was distilled off
  4. additionether was added to the cool mixture
  5. washAfter washing with dilute sodium hydroxide solution
  6. dry with materialwater, the ether solution was dried
  7. customevaporated to dryness
  8. distillationdistilled
  9. customThe product was collected at 110°-116°

Sources & evidence

ORD record
ord-d70fea656dfc4dd2a8e3c7cf3700a245
Source dataset
uspto-grants-1978_11
Patent number
US04124723

Linked notes

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