p-Toluenesulfonic acid → HCID 22670698, compound

HRID 1007667Notes

Reaction equation

HRID 1007667 reaction equation
[C:1]1([S:7][CH2:8][CH:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][CH:17](O)[CH:18]=[CH2:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:12]([C:9]([CH2:8][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:16]/[CH:17]=[CH:18]/[CH3:19])[CH:10]=[O:11])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 22670692HCID 22670692, compound

Product 1

HCID 22670698HCID 22670698, compound

Procedure

2-(Phenylthiomethyl)hexanal (2.67 g, 12 mmol), 3-buten-2-ol (5 mL, 58 mmol), and p-toluenesulfonic acid (0.05 g, 0.26 mmol) are added to 25 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 diluted with ethyl acetate, which is washed saturated NaHCO3 solution, brine, and dried with MgSO4. After removing solvents, the crude product is purified by chromatography. The product is obtained in 78.6% as a colorless oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. customto collect water
  4. additiondiluted with ethyl acetate, which
  5. washis washed saturated NaHCO3 solution, brine
  6. dry with materialdried with MgSO4
  7. customAfter removing solvents
  8. customthe crude product is purified by chromatography
  9. customThe product is obtained in 78.6% as a colorless oil

Sources & evidence

ORD record
ord-859505f77f484abab1ab3f92f84f17fd
Source dataset
uspto-grants-2004_09
Patent number
US06794544B2

Reaction notes

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