Sodium Hydroxide → 4-Cyclopropyl-2-ethyl-5-iodobenzoic acid

HRID 541370Notes

Reaction equation

[CH:1]1([C:4]2[C:13]([I:14])=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH2:15][CH3:16])[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[C:13]([I:14])=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH2:15][CH3:16])[CH:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 4-cyclopropyl-2-ethyl-5-iodobenzoate (compound 226.4, 2.50 g, 7.57 mmol, 1.00 equiv) in methanol (40 mL) was added aqueous sodium hydroxide (3.10 g, 77.5 mmol, 10.0 equiv, in 10 mL water). The resulting mixture was stirred for 15 h at 60° C. in an oil bath. After cooling to ambient temperature, the organic solvent was removed under reduced pressure and pH of the remaining aqueous layer was adjusted to 4 with hydrogen chloride (aq, 1 M). The solids were collected by filtration and dried in an oven under reduced pressure to yield 2.20 g (92%) of 4-cyclopropyl-2-ethyl-5-iodobenzoic acid as a white solid.

Workup

temperatureAfter cooling to ambient temperature
customthe organic solvent was removed under reduced pressure and pH of the remaining aqueous layer
filtrationThe solids were collected by filtration
customdried in an oven under reduced pressure

Sources & evidence

ORD record: ord-0e2b08c945114a4f9d74168d5d0673df
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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