Sodium Hydroxide → 2-Ethyl-5-iodo-4-methylbenzoic acid

HRID 541337Notes

Reaction equation

[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]([I:14])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6])[CH3:2].[OH-].[Na+]>CO.O>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]([I:14])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a round-bottom flask, was added a solution of methyl 2-ethyl-5-iodo-4-methylbenzoate (compound 211.2, 10.0 g, 32.9 mmol, 1.00 equiv) in methanol (40 mL). A solution of NaOH (5.26 g, 132 mmol, 4.00 equiv) in water (20 mL) was added dropwise. After stirring for 12 h at 40° C., the organic solvent was removed under reduced pressure. The pH of the remaining aqueous phase was adjusted to 4 with hydrogen chloride (aq., 6 M), then extracted with 2×100 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 9.30 g (97%) of 2-ethyl-5-iodo-4-methylbenzoic acid as a white solid.

Workup

customthe organic solvent was removed under reduced pressure
extractionextracted with 2×100 mL of ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThis resulted in 9.30 g (97%) of 2-ethyl-5-iodo-4-methylbenzoic acid as a white solid

Sources & evidence

ORD record: ord-37c052c34d2d4bb199b1ed4ac5a23596
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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