Toluene → HCID 45122014, compound

HRID 226201Notes

Reaction equation

HRID 226201 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH:8]=[CH2:9])[C:3]([OH:5])=[O:4].[C:10]1(C)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1>O>[CH2:6]([CH:2]1[O:1][C:15](=[O:24])[CH:14]([CH2:13][CH2:12][CH:11]=[CH2:10])[O:4][C:3]1=[O:5])[CH2:7][CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 57019543HCID 57019543, compound

Product 1

HCID 45122014HCID 45122014, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1-L flask equipped with a reflux condenser and a Dean-Stark trap, 3.0 g of 2-hydroxy-5-hexenoic acid, 400 ml of toluene and 30 mg of p-toluenesulfonic acid were added and refluxed under a nitrogen atmosphere. Water accumulated in the trap was eliminated from time to time. The mixture was cooled after refluxing for 72 hours. It was washed twice with 10 ml of a saturated aqueous solution of sodium hydrogencarbonate, and an obtained crude product was vacuum distilled in the presence of zinc oxide to obtain 1.06 g of desired 3,6-di(3-butenyl)-1,4-dioxane-2,5-dione (yield 41%).

Workup

  1. customIn a 1-L flask equipped with a reflux condenser
  2. temperaturerefluxed under a nitrogen atmosphere
  3. temperatureThe mixture was cooled
  4. temperatureafter refluxing for 72 hours
  5. washIt was washed twice with 10 ml of a saturated aqueous solution of sodium hydrogencarbonate
  6. customan obtained crude product
  7. distillationdistilled in the presence of zinc oxide

Sources & evidence

ORD record
ord-afc0acd40ba24d82a3167300d63e9864
Source dataset
uspto-grants-2009_07
Patent number
US07557176B2

Reaction notes

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