Benzene → 2-Decanone

HRID 1589290

Reaction equation

HRID 1589290 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.[Ru](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2](=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 133811-Decene

Product 1

HCID 127412-DecanoneYield 64%

Reagents, catalysts & solvents 3

HCID 8152Dodecyltrimethylammonium chlorideCatalystHCID 61482Cupric chloride dihydrateCatalystHCID 11007548Dichlorotris(triphenylphosphine)rutheniumCatalyst

Procedure

A mixture of copper (11) chloride dihydrate [10 mmol] and tris (triphenylphosphine) ruthenium (11) 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 64% 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-487f29c94b494518bfa7de0a0f2e8164
Source dataset
uspto-grants-1986_02
Patent number
US04568770

Linked notes

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