Sodium Hydroxide → 4-Cyclobutyl-3-iodobenzoic acid

HRID 1487852Notes

Reaction equation

HRID 1487852 reaction equation
[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=2[I:15])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=2[I:15])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68288885Methyl 4-cyclobutyl-3-iodobenzoate2×

Product 1

HCID 682885914-Cyclobutyl-3-iodobenzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-cyclobutyl-3-iodobenzoate (compound 9.2, 11.0 g, 34.8 mmol) and sodium hydroxide (4.00 g, 100 mmol) in methanol (100 mL) and water (50 mL) was stirred at 50° C. overnight. After cooling to ambient temperature, the volatile solvent was removed under reduced pressure. The residual aqueous material was washed with ethyl acetate (20 mL). The pH of the aqueous was then adjusted to 3-4 with aqueous hydrogen chloride (6 M). The resulting precipitate was collected by filtration and dried to yield the title compound as a white solid (8.60 g, 82%).

Workup

  1. customthe volatile solvent was removed under reduced pressure
  2. washThe residual aqueous material was washed with ethyl acetate (20 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-cbe5a96d9de846328bfcdbe4ae5c3855
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…