Sulfuric Acid → Methyl 5-iodo-2-isopropyl-4-methylbenzoate

HRID 541313Notes

Reaction equation

[CH:1]([C:4]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([CH3:3])[CH3:2].[I-].[I:16]([O-])(=O)(=O)=O.[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[I:16][C:11]1[C:12]([CH3:14])=[CH:13][C:4]([CH:1]([CH3:3])[CH3:2])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

To a round-bottom flask, was added a solution of methyl 2-isopropyl-4-methylbenzoate (compound 196.1, 6.50 g, 33.8 mmol, 1.00 equiv) in acetic acid (60 mL). Iodide (9.50 g, 37.4 mmol, 1.10 equiv), sodium periodate (3.60 g, 16.8 mmol, 0.50 equiv), and sulfuric acid (0.500 g, 0.15 equiv) were added to the reaction mixture. The resulting solution was stirred overnight at 100° C. After cooling to room temperature, the reaction was quenched with Na2S2O3 (aq., sat.). The mixture extracted with 3×100 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. This resulted in 6.00 g (56%) of methyl 5-iodo-2-isopropyl-4-methylbenzoate as a yellow oil.

Workup

temperatureAfter cooling to room temperature
customthe reaction was quenched with Na2S2O3 (aq., sat.)
extractionThe mixture extracted with 3×100 mL of ethyl acetate
washThe combined organic layers were washed with 3×100 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThis resulted in 6.00 g (56%) of methyl 5-iodo-2-isopropyl-4-methylbenzoate as a yellow oil

Sources & evidence

ORD record: ord-7dfed10adc6a4480a5cc2d78624c36d9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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