Methyl iodide → 1-(2-Iodo-5-isopropoxy-4-methoxyphenyl)ethanol

HRID 41919Notes

Reaction equation

I[CH3:2].[I:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:8][C:5]=1[CH:6]=[O:7].[NH4+].[Cl-]>CCOCC>[I:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:8][C:5]=1[CH:6]([OH:7])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of Mg turnings (195 mg, 8.02 g·atom) in dry Et2O (3.0 mL) was stirred at 0° C. under a nitrogen atmosphere then treated, dropwise, with a solution of iodomethane (0.58 mL, 9.31 mmol) in dry Et2O (7.5 mL). After 0.5 h a solution of aldehyde 5 (1.00 g, 3.12 mmol) in dry Et2O (7.5 mL) was added, dropwise, and the ensuing mixture then allowed to warm to 18° C. Stirring was continued at this temperature for a further 1 h then the reaction mixture was treated with NH4Cl (5 mL of a 20% w/v aqueous solution) and Et2O (10 mL). The separated organic phase was washed with H2O (1×5 mL) then dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound 6 (1.05 g, quant.) as a pale-yellow oil.

Workup

additionthen treated
temperatureto warm to 18° C
stirringStirring
washThe separated organic phase was washed with H2O (1×5 mL)
dry with materialthen dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-60afc81687f042ee83f28b0ccd79cac1
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536157B2

Reaction notes

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