Sodium Iodide → HCID 23083032, compound

HRID 2422248Notes

Reaction equation

HRID 2422248 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2OCC[O:18]2)=[CH:13][CH:12]=1)O.Cl[Si](C)(C)C.[I-].[Na+].C(#N)C>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 67146635HCID 67146635, compound

Product 1

HCID 23083032HCID 23083032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2,6-dimethylphenyl)[4-(1,3-dioxolan-2-yl)phenyl]methanol (7.10 g), chlorotrimethylsilane (10.8 g), sodium iodide (15.0 g) and acetonitrile (50 mL) was stirred at 50° C. for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with 10% aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 7:3 by volume ratio) to give 4-(2,6-dimethylbenzyl)benzaldehyde as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with 10% aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 7:3 by volume ratio)

Sources & evidence

ORD record
ord-ca78debf2cc74da0ae63517d9e5b3483
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

Loading…