Mesityl oxide → HCID 12757216, compound

HRID 1680646Notes

Reaction equation

HRID 1680646 reaction equation
[C:1](=O)=O.[C:4](#N)[CH3:5].[CH2:7]([Mg]Br)[CH3:8].[O:11]=[C:12]([CH:14]=C(C)C)[CH3:13].[Cl-].[NH4+]>CCOCC>[CH3:1][C:4]([CH3:5])([CH2:7][CH3:8])[CH2:13][C:12](=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 8858Mesityl oxide2×HCID 25517Ammonium ChlorideHCID 86587134Acetonitrile dry iceHCID 178418443HCID 178418443, compound

Product 1

HCID 12757216HCID 12757216, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-37 °C

Procedure

Cuprous iodide (19.0 gms., 0.098 moles) is placed in 100 ml. of ether and the reaction cooled to -37° C. (dry ice-acetonitrile). Ethyl magnesium bromide (3.0 mole solution, in ether, 70 ml., 210 mmoles) is then added slowly. The addition takes place over a twenty-minute period, and during this time the temperature of the reaction is never allowed to exceed -30° C. The blackish solution is allowed to cool at -37° C. and mesityl oxide (10 gms., 0.102 mole) (in ether, 50 ml.) is added dropwise. Mesityl oxide is added at such a rate so as to keep the temperature of reaction less than or equal to -10° C. Fifteen minutes after the completion of the reaction the suspension is poured onto 250 ml. of a saturated ammonium chloride solution. The organic layer is separated from the aqueous layer extracted with (3×50 ml.) portions of ether. The ether layers are combined and dried over magnesium sulfate. The drying agent is removed by vacuum filtration and the solvent removed under reduced pressure to yield a yellow oil. The oil is distilled under reduced pressure and gives two fractions: Fraction two contains 5.3 gms. (42%) of the titled compound as a yellow oil. The carbon:hydrogen analyses are 73.19 to 12.10. The mass spectrum exhibits peak at 73 (molecular ion), 71, 70, 59, 58, 57, 55, 43, 41, and 29. NMR absorptions are observed at 0.85 to 1.05, 1.25, 2.15, and 2.35δ. Infrared absorptions are observed at 1715, 1465, 1360, 1150, cm-1.

Workup

  1. additionThe addition
  2. customto exceed -30° C
  3. customthe temperature of reaction less than or equal to -10° C
  4. customFifteen minutes after the completion of the reaction the suspension
  5. additionis poured onto 250 ml
  6. customThe organic layer is separated from the aqueous layer
  7. extractionextracted with (3×50 ml.) portions of ether
  8. dry with materialdried over magnesium sulfate
  9. customThe drying agent is removed by vacuum filtration
  10. customthe solvent removed under reduced pressure
  11. customto yield a yellow oil
  12. distillationThe oil is distilled under reduced pressure
  13. customgives two fractions

Sources & evidence

ORD record
ord-47d1c2abaabe477d9723253fde7bdc4a
Source dataset
uspto-grants-1981_06
Patent number
US04275069

Reaction notes

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