Water → Methyl 4-hydroxy-3-iodo-5-nitrobenzoate

HRID 348974

Reaction equation

HRID 348974 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[I:15]Cl.O>C(O)(=O)C>[OH:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[I:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24640Iodine chlorideHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Product 1

HCID 21086206Methyl 4-hydroxy-3-iodo-5-nitrobenzoateYield 91,075.398%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-hydroxy-3-nitrobenzoate (2.0 g) in acetic acid (15 mL) was added iodine monochloride (1.65 mg) in acetic acid, and the mixture was stirred at 100° C. for 1.5 h. After cooling to room temperature, the mixture was poured into water (200 mL), and stirred for 30 min. The mixture was filtered and washed with water and hexanes. The yellow powder was collected by filtration and dried in vacuum oven overnight to give 2.99 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 11.68, 8.81, 8.72, 3.96.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringstirred for 30 min
  3. filtrationThe mixture was filtered
  4. washwashed with water and hexanes
  5. filtrationThe yellow powder was collected by filtration
  6. customdried in vacuum oven overnight

Sources & evidence

ORD record
ord-ce3a917d547b4565ad207f5df577f15f
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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