Benzyl Chloride → HCID 1339289, compound

HRID 1085633Notes

Reaction equation

HRID 1085633 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+].C(OC(=O)C)C.CCCCCC>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 (60g, 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-2aea56c819b64f268f3c6bf88ef8e0ad
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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