Oxygen → Acetophenone

HRID 1976870Notes

Reaction equation

HRID 1976870 reaction equation
[CH3:1][CH:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ON1C(=O)C2=CC=CC=C2C1=O.C=CC.O=O.C1OC1C>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(#N)C1C=CC=CC=1>[C:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:9])[CH3:1]

Participants

8

Reactant 5

HCID 977OxygenHCID 6378Propylene OxideHCID 74091-PhenylethanolHCID 8252PropyleneHCID 10665N-Hydroxyphthalimide

Product 1

HCID 7410AcetophenoneYield 98%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 7505BenzonitrileSolvent

Procedure

To a mixture of 1 mole of α-phenethyl alcohol, 0.1 mole of N-hydroxyphthalimide, 1 mmol of cobalt (II) acetate and 1 l of benzonitrile was added 1.5 moles of propylene, and the resultant mixture was stirred at 80° C. under oxygen atmosphere (oxygen: 1 atm) for 6 hours. Gas chromatographic analysis of products in a reaction mixture revealed that 0.92 mole of propylene oxide was formed, and that acetophenone (yield 98%: on α-phenethyl alcohol basis) was produced. The conversion rate from (x-phenethyl alcohol was 99%.

Workup

  1. customwas formed

Sources & evidence

ORD record
ord-f26a89fe92bb47beb3b1f8d96b232338
Source dataset
uspto-grants-2001_05
Patent number
US06229023B1

Reaction notes

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