Sodium Iodide → 3-Benzylbenzaldehyde

HRID 1666782Notes

Reaction equation

HRID 1666782 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)O)[CH:9]=[CH:10][CH:11]=1.[I-].[Na+].ClC([SiH3])Cl>C(#N)C.CCOC(C)=O>[CH2:12]([C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 10824966(3-[1,3]Dioxolan-2-ylphenyl)phenylmethanolHCID 57353436(Dichloromethyl)silane

Product 1

HCID 131027433-Benzylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine (3-[1,3]dioxolan-2-ylphenyl)-phenyl-methanol (2.3 g, 8.7 mmol) and sodium iodide (5.3 g, 35.0 mmol) in acetonitrile (25 ml). Add dichloromethylsilane (2.1 ml, 17.4 mmol) via syringe. After 10 min, dilute with EtOAc and wash with water, saturated sodium bicarbonate, 10% sodium thiosulfate, and then brine. Dry the organic layers (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 9:1 hexane:EtOAc to give the title compound.

Workup

  1. washwash with water, saturated sodium bicarbonate, 10% sodium thiosulfate
  2. dry with materialDry the organic layers (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give a residue
  6. washChromatograph the residue eluting with 9:1 hexane

Sources & evidence

ORD record
ord-38b31453dde3432b87536d43adb33641
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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