Hydrochloric Acid → 3-(3,4-Dimethoxyphenyl)propane-1-thiol

HRID 223230Notes

Reaction equation

HRID 223230 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13]O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].NC(N)=[S:17].[OH-].[Na+].Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][SH:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 775283-(3',4'-Dimethoxyphenyl)-1-propanolHCID 2723790Thiourea

Product 1

HCID 205230623-(3,4-Dimethoxyphenyl)propane-1-thiolYield 12.4%

Procedure

A mixture of 5.00 g (25.5 mmoles) of 3-(3,4-dimethoxyphenyl)propanol, 1.94 g (25.5 mmoles) of thiourea, and 8.5 ml of 48% hydrobomic acid is heated on steam bath for 1 hour, allowed to stand overnight at room temperature, and then heated again on a steam bath for 2 hours. After cooling, the reaction mixture is treated with 76.5 ml of 1 M sodium hydroxide and heated on the steam bath for 11/2 hours. After cooling, the reaction mixture is made acidic with 1 N hydrochloric acid and extracted with methylene chloride (followed by a brine wash). Silica gel chromatography using 10% ethyl acetate/Skellysolve B as eluent gives 0.67 g of 3-(3,4-dimethoxyphenyl)-1-propanethiol.

Workup

  1. temperatureis heated on steam bath for 1 hour
  2. temperatureheated again on a steam bath for 2 hours
  3. temperatureAfter cooling
  4. temperatureheated on the steam bath for 11/2 hours
  5. temperatureAfter cooling
  6. extractionextracted with methylene chloride (
  7. washwash)

Sources & evidence

ORD record
ord-e144c6adc4ba4f009c73d440c2bb483e
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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