Benzyl Chloride → HCID 1339289, compound

HRID 982480Notes

Reaction equation

HRID 982480 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:9][C:10]1[C:11]([OH:20])=[C:12]([O:18][CH3:19])[CH:13]=[C:14]([CH:17]=1)[CH:15]=[O:16].C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CN(C=O)C>[I:9][C:10]1[CH:17]=[C:14]([CH:13]=[C:12]([O:18][CH3:19])[C:11]=1[O:20][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:15]=[O:16]

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-HCID 21226206Ethyl acetate hexane

Product 1

HCID 1339289HCID 1339289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl chloride (30 g, 0.24 mol) was added to a solution of 5-iodovanillin (60 g, 0.216 mol) in DMF (250 mL) containing potassium carbonate (50 g). The mixture was stirred at 80° C. for 1.5 h or until TLC (hexane-ethyl acetate; 4:1, v/v; Rf 0.5) showed the reaction to be complete. The mixture was then cooled and the solvent was decanted into ice-water (1 L). The product was extracted with ethyl ether and the ethereal layer was washed with water, dried, and evaporated in vacuo to an oil, which solidified upon standing: mp 53°-54° C.

Workup

  1. customthe reaction
  2. temperatureThe mixture was then cooled
  3. customthe solvent was decanted into ice-water (1 L)
  4. extractionThe product was extracted with ethyl ether
  5. washthe ethereal layer was washed with water
  6. customdried
  7. customevaporated in vacuo to an oil, which

Sources & evidence

ORD record
ord-67cb406083f54776bd87b9d0d6159c00
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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