Mesitylene → HCID 21666955, compound

HRID 2231849Notes

Reaction equation

HRID 2231849 reaction equation
[F:1][C:2]([F:6])([F:5])[CH:3]=[CH2:4].[C]=O.[H][H].[CH2:11]([O:13][C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15])[CH3:12].[C:36]1(C)C=C(C)C=C(C)C=1>C(Cl)Cl>[CH2:11]([O:13][C:14](=[O:15])/[CH:16]=[CH:36]/[CH2:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH3:12]

Participants

7

Reactant 5

HCID 7947MesityleneHCID 126723,3,3-TrifluoropropeneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 21666955HCID 21666955, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

Analogously to J. Am. Chem. Soc. 104, 3527-29 (1982), 3.42 g (10 mmol) of Co2 (CO)8 in 50 ml of mesitylene are placed in a 0.3 liter autoclave at 0°; 0.5 mol of 3,3,3-trifluoropropene are introduced, followed at room temperature in succession by 65 bars of carbon monoxide and 65 bars of hydrogen. The reaction mixture is heated to 110° C. and, by the addition of a (1:1) mixture (v/v) of CO and H2, the pressure is maintained constant at 130 bar. After absorption of the theoretical amount of the CO/H2 mixture (1-5 hours), the whole is cooled to 0° and the autoclave is returned to normal pressure. To the crude mixture, which has been rinsed out with a small amount of mesitylene, there is slowly added, at room temperature, a solution of 156.8 g (0.45 mol) of ethoxycarbonylmethylenetriphenylphosphorane in 600 ml of methylene chloride. After the mildly exothermic reaction has subsided, the whole is stirred at room temperature for 21/2 hours and then concentrated by evaporation. The residue is made into a slurry with pentane (approx. 100 ml), precipitated triphenylphosphine oxide is removed, and then distillation at reduced pressure is carried out. The desired ester is obtained in the form of a colourless oil (b.p. 78°-82°/26 mm Hg) in a yield of 50%.

Workup

  1. customare placed in a 0.3 liter autoclave at 0°
  2. temperaturethe pressure is maintained constant at 130 bar
  3. customAfter absorption of the theoretical amount of the CO/H2 mixture (1-5 hours)
  4. temperaturethe whole is cooled to 0°
  5. washTo the crude mixture, which has been rinsed out with a small amount of mesitylene, there
  6. additionis slowly added, at room temperature
  7. customAfter the mildly exothermic reaction
  8. concentrationconcentrated by evaporation
  9. customprecipitated triphenylphosphine oxide
  10. customis removed
  11. distillationdistillation at reduced pressure

Sources & evidence

ORD record
ord-f3003c505f0b48a5b085a35edeebfbec
Source dataset
uspto-grants-1988_11
Patent number
US04785004

Reaction notes

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