Benzene → 16282-50-1

HRID 2164067Notes

Reaction equation

HRID 2164067 reaction equation
[I-].[H-].[Na+].[O:4]1[CH2:6][CH2:5]1.[C:7]1(C)[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.B(F)(F)F.CCOCC.[CH:27]1[CH:32]=[CH:31]C=CC=1>>[CH:31]1([CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[O:4])[CH2:32][CH2:27]1

Participants

7

Reactant 6

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 24758Sodium hydrideHCID 30165Iodide Ion

Product 1

HCID 1487126216282-50-1

Procedure

Reaction scheme 2 starts from the same cyclopropyl phenyl ketone but in the first step of the reaction, the ketone is reacted with dimethyloxosulphonium methylide, for example in dimethylsulphoxide for about 24 hours. The reagent used is an ylide of formula (CH3)2S+O-C-H2 which is obtainable by reacting dimethyl sulphoxide with methyl iodide to form a quaternary iodide and reacting the quaternary iodide with sodium hydride. The reaction with the ylide forms a stable oxirane intermediate which rearranges under the influence of heat and acid, for example by heating in benzene with p-toluene sulphonic acid or boron trifluoride etherate to form α-cyclopropyl-phenylacetaldehyde which can be oxidised to the corresponding acetic acid by a similar method to that described above.

Workup

  1. temperatureof heat

Sources & evidence

ORD record
ord-1d525578f7c442b48bcf79c9b34ac688
Source dataset
uspto-grants-1979_01
Patent number
US04137324

Reaction notes

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