Acetic Anhydride → HCID 67374420, compound

HRID 1805911Notes

Reaction equation

HRID 1805911 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14].[C:20]([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[C:13]([O:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:20])=[O:5])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178427895HCID 178427895, compound

Product 1

HCID 67374420HCID 67374420, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a stirred suspension of 2-hydroxy-5-iodo-3-methylbenzoate (1.24 g, 4.25 mmol) in neat acetic anhydride (1.803 mL, 19.10 mmol) was added a 3 drops of concentrated sulfuric acid (0.226 mL, 4.25 mmol). The resultant orange solution was stirred at room temperature overnight. The solution was diluted with 3% aqueous NaHCO3 (13 mL) and extracted with CHCl3 (3×30 mL). The combined organic phases were washed with water (4×20 mL), dried (MgSO4), and concentrated in vacuo to afford methyl 2-(acetyloxy)-5-iodo-3-methylbenzoate, as a colorless solid. 1H NMR (500 MHz, CHCl3): δ 8.17 (s, 1 H); 7.78 (s, 1 H); 3.89 (s, 3 H); 2.25 (s, 3 H); 2.21 (s, 3 H).

Workup

  1. extractionextracted with CHCl3 (3×30 mL)
  2. washThe combined organic phases were washed with water (4×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c275474b0a94b5d880f0800a23b8ba8
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

Loading…