Thiophenol → HCID 428841, compound

HRID 462249Notes

Reaction equation

HRID 462249 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:13]C)(=[O:12])/[CH:9]=[CH:10]/[CH3:11].[OH-].[Na+]>CO.O.[Na]>[C:1]1([S:7][CH:10]([CH3:11])[CH2:9][C:8]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 638132Methyl Crotonate

Product 1

HCID 428841HCID 428841, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 5360545SodiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

0.25 g of sodium in small pieces, in 50 ml (0.5 mol) of thiophenol, is heated to 90°-95° C whilst stirring, and 52.5 ml (0.55 mol) of methyl crotonate are added dropwise. The mixture is heated further for 1 hour at 120° C and 85 g (boiling point/5 mm Hg = 137°-138° C) of the resulting ester are distilled in vacuo. 53 g (0.25 mol) of this ester in solution in 200 ml of methanol are hydrolysed with 16 g (0.4 mol) of NaOH in 200 ml of water. The mixture is heated for 2 hours under reflux, the alcohol is evaporated in vacuo, the residue is taken up in water and the product is precipitated with concentrated HCl and extracted with ether. The extract is washed with water and dried, and 32 g (65%) of a white oil are obtained.

Workup

  1. distillation85 g (boiling point/5 mm Hg = 137°-138° C) of the resulting ester are distilled in vacuo
  2. temperatureThe mixture is heated for 2 hours
  3. temperatureunder reflux
  4. customthe alcohol is evaporated in vacuo
  5. customthe product is precipitated with concentrated HCl
  6. extractionextracted with ether
  7. washThe extract is washed with water
  8. customdried

Sources & evidence

ORD record
ord-77f1b82a778142ecaeab94c5128687bd
Source dataset
uspto-grants-1977_12
Patent number
US04065584

Reaction notes

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