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

HRID 541345Notes

Reaction equation

HRID 541345 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]([CH2:16][CH3:17])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:5]2[C:14]([I:15])=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH2:16][CH3:17])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68288985Methyl 4-cyclobutyl-2-ethyl-5-iodobenzoate2×

Product 1

HCID 682889094-Cyclobutyl-2-ethyl-5-iodobenzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a round-bottom flask, was added a solution of methyl 4-cyclobutyl-2-ethyl-5-iodobenzoate (compound 181.4, 10.3 g, 30.0 mmol, 1.00 equiv) in methanol (100 mL). A solution of sodium hydroxide (3.60 g, 3.00 equiv) in water (10 mL) was added dropwise to the stirred reaction mixture. The resulting mixture was stirred for 2 h at 60° C. After cooling to ambient temperature, the volatiles were removed under reduced pressure. The pH of the remaining aqueous mixture was adjusted to ˜4 using HCl (aq., 1 M). The resulting precipitate was collected by filtration and dried to yield 9.00 g (91%) of 4-cyclobutyl-2-ethyl-5-iodobenzoic acid as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe volatiles were removed under reduced pressure
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-81ba5a0af4e243d9bfbd6f1bea331531
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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