Dimethyl Sulfoxide → 4-Benzyloxy-2-iodo-5-methoxybenzoic acid

HRID 2381233Notes

Reaction equation

HRID 2381233 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([I:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=[O:22].S(=O)(=O)(O)O.Cl([O-])=O.[Na+]>O.C(#N)C>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([C:13]([OH:22])=[O:14])=[C:11]([I:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1118Sulfuric AcidHCID 127730874-Benzyloxy-2-iodo-5-methoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 583455814-Benzyloxy-2-iodo-5-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-benzyloxy-2-iodo-5-methoxybenzaldehyde (reference example 1-1) (20 g), dimethylsulfoxide (19 mL), concentrated sulfuric acid (3 mL), water (30 mL) and acetonitrile (181 mL) was added a mixture of sodium chlorite (9.8 g) and water (30 mL). After stirring at room temperature for 30 minutes, water was added to the mixture. Insoluble materials were collected by filtration to give the title compound (20.3 g).

Workup

  1. additionwas added
  2. filtrationInsoluble materials were collected by filtration

Sources & evidence

ORD record
ord-b43f4da8e86247cfa1d44d64e56f4b32
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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