Water → 2-(2-Iodo-5-methoxyphenyl)acetic acid

HRID 543425

Reaction equation

HRID 543425 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[I:13]Cl.O>C(O)(=O)C.II>[I:13][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 15719(3-Methoxyphenyl)acetic acidHCID 24640Iodine chloride

Product 1

HCID 8200712-(2-Iodo-5-methoxyphenyl)acetic acidYield 65%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 45 g (0.27 mole) of 3-methoxybenzeneacetic acid, 52.6 g (0.32 mole) of iodine monochloride and 1 g of iodine was allowed to stand in 500 ml of glacial acetic acid for six days at room temperature. The reaction was poured into water and the solid collected. It was recrystallized from toluene to give 51 g of crystalline 2-iodo-5-methoxybenzeneacetic acid, mp 133.5°-134.5° C. (65% yield).

Workup

  1. customthe solid collected
  2. customIt was recrystallized from toluene

Sources & evidence

ORD record
ord-b4f7f8a97a8e42fb9576438e9b94f03a
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Linked notes

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