p-Toluenesulfonic acid → HCID 22670697, compound

HRID 1355429Notes

Reaction equation

HRID 1355429 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O[CH:20]([CH:22]=[CH2:23])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:15]([C:12]([CH2:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])([CH2:21]/[CH:20]=[CH:22]/[CH3:23])[CH:13]=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 14640309HCID 14640309, compound

Product 1

HCID 22670697HCID 22670697, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-(((4-methylphenyl)-sulfonyl)methyl)hexanal (5.63 g, 21 mmol) in 35 ml of toluene in a RBF fitted with a Dean-Stark trap is added 2-hydroxy-3-butene (10 mL, 115 mmol), followed by p-toluenesulfonic acid (0.13 g) at room temperature under nitrogen. The mixture is heated to reflux overnight. After cooling to room temperature, the toluene solution is washed with saturated NaHCO3 solution (2×10 mL), water (2×20 mL), brine (1×20 mL), and dried with MgSO4. After removing solvents, the product is obtained as a brownish oil in quantitative yield with a GC purity of 89%.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. washthe toluene solution is washed with saturated NaHCO3 solution (2×10 mL), water (2×20 mL), brine (1×20 mL)
  4. dry with materialdried with MgSO4
  5. customAfter removing solvents
  6. customthe product is obtained as a brownish oil in quantitative yield with a GC purity of 89%

Sources & evidence

ORD record
ord-966d6eb3a3b042f4a02d10a4367cb793
Source dataset
uspto-grants-2003_07
Patent number
US06586434B2

Reaction notes

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