p-Toluenesulfonic acid → HCID 22670708, compound

HRID 1355427Notes

Reaction equation

HRID 1355427 reaction equation
[CH3:1][CH:2]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:3]=[O:4].[CH3:13][CH:14](O)[CH:15]=[CH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:1][C:2]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH2:13]/[CH:14]=[CH:15]/[CH3:16])[CH:3]=[O:4]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 110739982-Methyl-3-(phenylsulfanyl)propanal

Product 1

HCID 22670708HCID 22670708, compound

Procedure

2-Methyl-3-phenylthiopropanal (9.07 g, 0.05 mole), 3-buten-2-ol (18.04 g, 0.25 mole), and p-toluenesulfonic acid (0.24 g, 0.0013 mole) are added to 90 ml of xylenes. The reaction mixture is heated to reflux using a Dean-Stark trap to collect water. After 3 hours, the mixture is cooled to room temperature and quenched with 30 ml of saturated NaHCO3 solution. The two phases are separated and the aqueous phase is extracted with 30 ml of ethyl acetate. The combined organic extracts is washed with 20 ml of brine and dried with Na2SO4. After removing solvents, the crude product is purified by chromatography. The product is obtained in 74.3% as a colorless oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. customto collect water
  4. customquenched with 30 ml of saturated NaHCO3 solution
  5. customThe two phases are separated
  6. extractionthe aqueous phase is extracted with 30 ml of ethyl acetate
  7. washThe combined organic extracts is washed with 20 ml of brine
  8. dry with materialdried with Na2SO4
  9. customAfter removing solvents
  10. customthe crude product is purified by chromatography
  11. customThe product is obtained in 74.3% as a colorless oil

Sources & evidence

ORD record
ord-b9c45d0abce14f5f8baefa990e59b857
Source dataset
uspto-grants-2003_07
Patent number
US06586434B2

Reaction notes

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