3-Buten-2-ol → HCID 22670696, compound

HRID 1355424Notes

Reaction equation

HRID 1355424 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:9][CH2:10][CH2:11][CH3:12])[CH:7]=[O:8])(=[O:3])[CH3:2].O[CH:14]([CH:16]=[CH2:17])[CH3:15].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>>[C:1]([S:4][CH2:5][C:6]([CH2:15][CH2:14][CH2:16][CH3:17])([CH2:9]/[CH:10]=[CH:11]/[CH3:12])[CH:7]=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 117163-Buten-2-olHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22670694HCID 22670694, compound

Product 1

HCID 22670696HCID 22670696, compoundYield 80.5%

Procedure

To a stirred solution of 2-(acetylthiomethyl)hexanal (32.6 g, 0.173 mole) in 325 ml of xylenes in a 500-mL RBF fitted with a Dean-Stark trap is added 2-hydroxy-3-butene (22.5 mL, 0.259 mole), followed by pyridinium p-toluenesulfonate (4.34 g, 0.017 mole) at room temperature under nitrogen. The mixture is heated to reflux overnight. After cooling to room temperature, the xylenes solution is washed with 300 mL of saturated NaHCO3 solution. The aqueous phase is extracted with 300 mL of ethyl acetate. The combined organic extract is washed with 200 mL of brine and 200 mL of water. After removing solvents, the product is obtained by vacuum distillation (157-160° C./1.5 mmHg) in 80.5% yield.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. washthe xylenes solution is washed with 300 mL of saturated NaHCO3 solution
  4. extractionThe aqueous phase is extracted with 300 mL of ethyl acetate
  5. extractionThe combined organic extract
  6. washis washed with 200 mL of brine and 200 mL of water
  7. customAfter removing solvents
  8. customthe product is obtained by vacuum distillation (157-160° C./1.5 mmHg) in 80.5% yield

Sources & evidence

ORD record
ord-03816ddcadd54aada4928ad3b56e4ccf
Source dataset
uspto-grants-2003_07
Patent number
US06586434B2

Reaction notes

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