Methyl Vanillate → Methyl 4-hydroxy-3-iodo-5-methoxybenzoate

HRID 423259Notes

Reaction equation

HRID 423259 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1.[I:14]N1C(=O)CCC1=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([O:11][CH3:12])[C:7]([OH:10])=[C:8]([I:14])[CH:9]=1

Participants

4

Reactant 2

HCID 19844Methyl VanillateHCID 120273N-Iodosuccinimide

Product 1

HCID 53426739Methyl 4-hydroxy-3-iodo-5-methoxybenzoateYield 113.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxy-3-methoxybenzoic acid methyl ester (5.0 g) in tetrahydrofuran (20 mL) was added N-iodosuccinimide (6.17 g) at 0° C., and the mixture was stirred for 1 hour. The precipitated solid was filtered, washed with water, and dried to give the title compound (9.60 g).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-91f5d4f170584cc5abefa9ba12bcba63
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

Loading…