Water → 3-tert-butyl-5-iodosalicylaldehyde

HRID 1965923Notes

Reaction equation

HRID 1965923 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([CH:8]=[O:9])[C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2].[I:14](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.O>CO.C(Cl)Cl>[C:1]([C:5]1[CH:12]=[C:11]([I:14])[CH:10]=[C:7]([CH:8]=[O:9])[C:6]=1[OH:13])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 36786753-tert-Butyl-2-hydroxybenzaldehydeHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 120345043-tert-butyl-5-iodosalicylaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-tert-butyl salicylaldehyde (1) (8.4 mmol) was dissolved in 100 ml of a mixture of methanol and methylene chloride (3:7). Benzyltrimethylammonium dichloroiodate (3.23 g; 9.2 mmol) and water free calcium carbonate (1.1 g; 11 mmol) were added. After two hours, the excess of calcium carbonate was filtered off. After removal of about 80% of the solvent, 20 ml of a sodium hydrogensulfite solution (5%) was added decolourizing the mixture. Extraction with diethyl ether, drying over sodium sulphate and removal of the solvent yielded the aldehyde as raw product. Purification by recrystallization from n-pentane produced 3-tert-butyl-5-iodosalicylaldehyde in a 48% yield as yellow crystals which are slightly light sensitive and should be stored in the dark.

Workup

  1. filtrationthe excess of calcium carbonate was filtered off
  2. customAfter removal of about 80% of the solvent, 20 ml of a sodium hydrogensulfite solution (5%)
  3. additionwas added
  4. extractionExtraction with diethyl ether
  5. dry with materialdrying over sodium sulphate and removal of the solvent

Sources & evidence

ORD record
ord-1a2034d00123467f8753b696c71e2e3f
Source dataset
uspto-grants-2013_04
Patent number
US08420563B2

Reaction notes

Loading…