Hydrochloric Acid → HCID 22313365, compound

HRID 965828Notes

Reaction equation

HRID 965828 reaction equation
[O-]CC.[Ca+2].[O-]CC.[CH2:8]1[O:12][CH:9]1[CH2:10][CH3:11].[I:13][C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:15]=1[OH:21].Cl>>[I:13][C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:8][CH:9]([OH:12])[CH2:10][CH3:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 78341,2-EpoxybutaneHCID 72858Phenol, 2,4-diiodo-HCID 6451473Calcium diethanolate

Product 1

HCID 22313365HCID 22313365, compoundYield 67%

Conditions

Temperature
80 °C

Procedure

A suspension of calcium ethoxide (816 mg, 6.3 mmol), butene oxide (5.2 mL, 93 mmol) and 2,4-diiodophenol (2.17 g, 6.3 mmol) is heated in a sealed flask at 80° C. for 18 h. The reaction mixture is allowed to cool, poured into 1N HCl and extracted three times with CH2Cl2. The combined organic extracts are dried (Na2SO4), filtered and concentrated in vacuo. The resulting material is purified by column chromatography (two columns, step gradient of 30-40-50% CH2Cl2 in hexanes) to give 1-(2,4-diiodophenoxy)butan-2-ol as a clear oil (1.73 g, 67%).1H NMR (400 MHz, CDCl3) δ 8.04, 7.56, 6.57, 4.03, 3.9, 3.84, 2.42, 1.65, 1.04.

Workup

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe combined organic extracts are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material is purified by column chromatography (two columns, step gradient of 30-40-50% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-bed01c683b224cb58643c9f760f653fd
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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