Methyl iodide → 2-Isopropylanisole

HRID 393395Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].CI.[C:13](=O)([O-])[O-].[K+].[K+]>>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:13])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 69432-Isopropylphenol

HCID 11430Potassium Carbonate

Product 1

HCID 2706232-Isopropylanisole

Procedure

2-Isopropylphenol was reacted with methyl iodide in the presence of potassium carbonate to yield 1-isopropyl-2-methoxybenzene, which in turn was reacted with the solution of unisolated intermediate (CF3CO2)3 I described above to form the bis-[3-isopropyl-4-methoxyphenyl] iodonium salt in 40-70% yield. The bis-[3-isopropyl-4-methoxyphenyl] iodonium salt precipitated as a gummy solid, making purification impracticable and contributing to the unpredictability of the yield.

Sources & evidence

ORD record: ord-28edfda2f28c48e495cedc76ca0b3eb7
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806381B2

Reaction notes

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