Hydrochloric Acid → Methyl 4-Iodophenylacetate

HRID 2402426Notes

Reaction equation

HRID 2402426 reaction equation
Cl.[I:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.O1CCOC[CH2:14]1>CO>[I:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1372144-Iodophenylacetic acid

Product 1

HCID 10378700Methyl 4-Iodophenylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4M solution of HCl in dioxane (50 mL) was added to 2-(4-iodophenyl)acetic acid (10 g, 38.2 mmol) in MeOH (100 mL) and the reaction stirred overnight. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with 0-30% EtOAc in hexanes to afford methyl 2-(4-iodophenyl)acetate in 10.42 g (99%). LRMS: 276.0 (calc) 277.1 (found)(MH+)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-d5d326ec55a242bd931b93cea2a4cd52
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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