Toluene → HCID 54102009, compound

HRID 573494Notes

Reaction equation

HRID 573494 reaction equation
[PH4+].[C:2]1([CH3:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-:10].[K+].[K+].[CH:15](=O)/[CH:16]=C/C>O>[C:9]([O:10][CH2:15][CH3:16])(=[O:12])[CH2:3][CH2:4][CH:5]=[CH:6][CH:7]=[CH:2][CH3:8]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 447466CrotonaldehydeHCID 5460504Phosphonium

Product 1

HCID 54102009HCID 54102009, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Next, in a stream of nitrogen, the phosphonium salt (b) (420 g, 0.92 mol), toluene (1600 ml), potassium carbonate (506.2 g, 3.66 mol), and crotonaldehyde (256.7 g, 3.66 mol) were put into a 5-L flask, followed by stirring at 65° C. for 7 hours. The reaction solution was cooled to room temperature, and water (840 g) was put thereinto, followed by stirring for 30 minutes, and then subjected to separation of liquid. The solvent was evaporated from the organic layer under a reduced pressure. A solid thus precipitated was removed by filtration. This solution was distilled under a reduced pressure (65 to 70° C./1.5 torr), and ethyl 4,6-octadienoate (c) was obtained (114.4 g, yield 74%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringby stirring for 30 minutes
  3. customsubjected to separation of liquid
  4. customThe solvent was evaporated from the organic layer under a reduced pressure
  5. customA solid thus precipitated
  6. customwas removed by filtration
  7. distillationThis solution was distilled under a reduced pressure (65 to 70° C./1.5 torr)

Sources & evidence

ORD record
ord-d2309b1d195b4e4ea8b719d5727d0844
Source dataset
uspto-grants-2015_05
Patent number
US09029593B2

Reaction notes

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