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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 81751Generated: October 25, 2026

Methyl iodide → 1-Chloro-4-isopropyl-2-methoxybenzene

https://huagongshe.com/reaction/81751

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantPotassium CarbonateHCID 11430—
Reactant4-Chloro-3-isopropylphenolHCID 18327844—
Reactant2-Chloro-5-isopropylphenolHCID 59596487—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product1-Chloro-4-isopropyl-2-methoxybenzeneHCID 58928056—
Product1-Chloro-2-isopropyl-4-methoxy-benzeneHCID 58977025—

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of 2-chloro-5-isopropyl-phenol and 4-chloro-3-isopropyl-phenol from step 1 (8.694 g, 47.1 mmol) in 50 mL DMF was added K2CO3. Iodomethane (3.5 mL, 56.5 mmol) was added and the mixture was warmed to 50° C. After 4 hours H2O was added. The mixture was extracted with ethyl acetate, washed with H2O, washed and washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give 1-chloro-4-isopropyl-2-methoxy-benzene and 1-chloro-2-isopropyl-4-methoxy-benzene (9.289 g) as a 7:3 inseparable mixture in the form of a pale yellow oil, which was used directly in the following step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846705B2
Source datasetuspto-grants-2014_09
ORD IDord-3b7131fca7064fffac7894f87ece74f2
Source noteuspto-grants-2014_09