Methyl iodide → 4,5-Dihydro-3,4,4-trimethyloxazolium iodide

HRID 568916Notes

Reaction equation

HRID 568916 reaction equation
C(C1C=CC(CCCCC2C=CC=CC=2[C:21]2[O:22][CH2:23][C:24]([CH3:27])([CH3:26])[N:25]=2)=CC=1)CCC.[CH3:28][I:29]>>[I-:29].[CH3:28][N+:25]1[C:24]([CH3:27])([CH3:26])[CH2:23][O:22][CH:21]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 198479512-[2-(4-(4-Butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline

Product 1

HCID 118173244,5-Dihydro-3,4,4-trimethyloxazolium iodide

Procedure

Following the procedures of Example 1(a), (b) and (c), to 4-(4-butylphenyl)butylmagnesium bromide (from 21.47 mmoles of 4-(4-butylphenyl)butyl bromide and 18.96 mmoles of magnesium) in distilled tetrahydrofuran (35 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (16.32 mmoles) in tetrahydrofuran (15 ml). Workup of the reaction mixture furnished 2-[2-(4-(4-butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline as an oil. A solution of the oxazoline (14.41 mmoles) in methyl iodide (20 ml) was refluxed under argon for 18 hours. Removal of the volatiles afforded the corresponding 3,4,4-trimethyloxazolinium iodide as a white solid (mp 91°-94° C.). To an ice cold solution of the iodide (14.07 mmoles) in methanol was added in portions sodium borohydride (14.30 mmoles). Similar treatment of the reaction mixture resulted in the isolation of the desired benzaldehyde product as an oil.

Workup

  1. customRemoval of the volatiles

Sources & evidence

ORD record
ord-3d92af277f2b406cbb2912e5a6ba6924
Source dataset
uspto-grants-1988_03
Patent number
US04730005

Reaction notes

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