Benzene → 2-Decanone

HRID 1589289

Reaction equation

HRID 1589289 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1C=CC=CC=1.[OH2:17]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCC.O.O.[Cu](Cl)Cl.[Pd](Cl)Cl>[CH3:1][C:2](=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:1][CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 133811-Decene

Product 2

HCID 127412-DecanoneHCID 32899trans-2-Decene

Reagents, catalysts & solvents 3

HCID 8152Dodecyltrimethylammonium chlorideCatalystHCID 24290Palladium ChlorideCatalystHCID 61482Cupric chloride dihydrateCatalyst

Procedure

A mixture of copper (II) chloride dihydrate [10 mmol] and palladium (II) chloride [1.0 mmol] in water [10 ml] was stirred for 10 minutes at room temperature. Then 1-decene [3.51 g, 25 mmol] was added followed by benzene [15 ml] and dodecyltrimethylammonium chloride [2.0 mmol]. Oxygen was bubbled through the solution at 80° C. for 48 hours. After cooling to room temperature, ethyl acetate (15 ml) was added and the solution was filtered. The filtrate was dried using anhydrous magnesium sulphate, and then distilled to provide pure 2-decanone in 75% yield and 2-decene in 2% yield.

Workup

  1. customOxygen was bubbled through the solution at 80° C. for 48 hours
  2. temperatureAfter cooling to room temperature
  3. additionethyl acetate (15 ml) was added
  4. filtrationthe solution was filtered
  5. customThe filtrate was dried
  6. distillationdistilled

Sources & evidence

ORD record
ord-7ba009f9c7a14492b560de5cbc51e7a1
Source dataset
uspto-grants-1986_02
Patent number
US04568770

Linked notes

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