Water → 4-Iodoresorcinol

HRID 494844Notes

Reaction equation

HRID 494844 reaction equation
[I:1]Cl.[C:3]1([CH:10]=[CH:9][CH:8]=[C:6]([OH:7])[CH:5]=1)[OH:4].O.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)C>[I:1][C:8]1[CH:9]=[CH:10][C:3]([OH:4])=[CH:5][C:6]=1[OH:7]

Participants

6

Reactant 4

HCID 962WaterHCID 5054ResorcinolHCID 24437Sodium SulfiteHCID 24640Iodine chloride

Product 1

HCID 6167384-IodoresorcinolYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of iodine monochloride (8.2 g, 50.5 mmol) in dry diethyl ether (100 mL) was added drop-wise over 45 minutes to a cold solution (0° C.) of resorcinol (5.5 g, 49.9 mmol) in dry ether (50 mL). After stirring at room temperature for one hour 100 mL of water and 1.0 g of sodium sulfite was added. The organic phase was separated and the aqueous phase was washed with 100 mL of ether, the combine ether phase was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified using flash chromatography over silica gel using a mixture of CH2Cl2:MeOH (100:1) to provide the title compound in 50% yield. 1HNMR (300 MHz, CDCl3) δ 4.95 (s, 1H), 6.23 (m, 1H), 6.55 (m, 1H), 7.43 (m, 1H). MS (CDI) m/z 237 (M+H)+.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washthe aqueous phase was washed with 100 mL of ether
  4. dry with materialthe combine ether phase was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. additiona mixture of CH2Cl2:MeOH (100:1)

Sources & evidence

ORD record
ord-7123cffd23354d90a2a57d047970ffdd
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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