p-Toluenesulfonic acid → HCID 22670707, compound

HRID 1355428Notes

Reaction equation

HRID 1355428 reaction equation
[Cl: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.C(OCC)(=O)C>[CH2:15]([C:12]([CH2:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])([CH2:21]/[CH:20]=[CH:22]/[CH3:23])[CH:13]=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 22670701HCID 22670701, compound

Product 1

HCID 22670707HCID 22670707, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(((4-chlorophenyl)-sulfonyl)methyl)hexanal (3.38 g, 11.73 mmol) in 30 ml of toluene in a RBF fitted with a Dean-Stark trap is added 2-hydroxy-3-butene (5 mL, 57.73 mmol), followed by p-toluenesulfonic acid (0.13 g) at room temperature under nitrogen. The mixture is heated to reflux for 20 hours. After cooling to room temperature, the toluene solution is diluted with 10 mL of ethyl acetate and washed with 10 mL of saturated NaHCO3 solution. The aqueous phase is extracted with ethyl acetate. The combined organic extract is washed with water (2×10 mL), brine (1×10 mL), and dried with MgSO4. After removing solvents, the product is obtained as a brownish oil in 98% yield.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 20 hours
  3. washwashed with 10 mL of saturated NaHCO3 solution
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. extractionThe combined organic extract
  6. washis washed with water (2×10 mL), brine (1×10 mL)
  7. dry with materialdried with MgSO4
  8. customAfter removing solvents
  9. customthe product is obtained as a brownish oil in 98% yield

Sources & evidence

ORD record
ord-958d401a6f5140c1b8c4e81b42b9dfa9
Source dataset
uspto-grants-2003_07
Patent number
US06586434B2

Reaction notes

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