p-Toluenesulfonic acid → HCID 22670698, compound

HRID 1355425Notes

Reaction equation

HRID 1355425 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-4978a018e0774f78b485ab846d55f7af
Source dataset
uspto-grants-2003_07
Patent number
US06586434B2

Reaction notes

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