Hydrochloric Acid → 3-Phenoxypropane-1-thiol

HRID 65421

Reaction equation

HRID 65421 reaction equation
[C:1]1([O:7][CH2:8][CH2:9][CH2:10]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC(N)=[S:14].[OH-].[K+].Cl>C(O)C.CO>[O:7]([CH2:8][CH2:9][CH2:10][SH:14])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68522Benzene, (3-bromopropoxy)-HCID 2723790Thiourea

Product 1

HCID 187927073-Phenoxypropane-1-thiolYield 61.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

160 g of 3-bromopropyl phenyl ether and 63 g of thiourea were dissolved in 300 ml of ethanol and the solution was refluxed with heating for 3 hours. A methanol solution containing 194 g of potassium hydroxide was added to the reaction solution and the mixture was stirred at 50° C. for 2 hours. The mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate followed by distillation under reduced pressure to obtain 76.5 g of 3-phenoxypropanethiol. A boiling point was 135° to 138° C. at 17 mm Hg.

Workup

  1. temperaturethe solution was refluxed
  2. temperaturewith heating for 3 hours
  3. additionwas added to the reaction solution
  4. extractionextracted with ethyl acetate
  5. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4750c884274143519e7a5c5c64cfe428
Source dataset
uspto-grants-1986_09
Patent number
US04614702

Linked notes

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