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

HRID 541377Notes

Reaction equation

[CH:1]1([C:5]2[C:14]([I:15])=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH3:16])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:5]2[C:14]([I:15])=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:16])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 4-cyclobutyl-5-iodo-2-methylbenzoate (compound 152.3, 35.0 g, 106 mmol, 1.00 equiv) in methanol (200 mL) at 0-5° C. was added dropwise aqueous sodium hydroxide (12.7 g, 318 mmol, 3.00 equiv in 100 mL water). The resulting mixture was stirred for 3 h at 60° C. After cooling to ambient temperature, the organic solvent was then removed under reduced pressure. The pH of the remaining aqueous phase was adjusted to ˜4 with hydrogen chloride (aqueous, 2 M). The resulting solids were collected by filtration and dried in an oven under reduced pressure to yield 31.0 g (93%) of the title compound as a white solid.

Workup

temperatureAfter cooling to ambient temperature
customthe organic solvent was then removed under reduced pressure
filtrationThe resulting solids were collected by filtration
customdried in an oven under reduced pressure

Sources & evidence

ORD record: ord-bca9b338b3d84e25834f3a496aff2af6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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