Benzyl Chloride → HCID 53926997, compound

HRID 1780014Notes

Reaction equation

HRID 1780014 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([OH:5])[CH:3]=1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21](=[O:24])([O-])[O-].[K+].[K+].C(N([CH2:32][CH3:33])CC)C>CN(C)C=O.O>[C:21]([O:12][CH2:1][C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([O:5][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1)(=[O:24])[C:33]1[CH:32]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 7503Benzyl Chloride2×HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 12575Isovanillic Acid

Product 1

HCID 53926997HCID 53926997, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

51 g of isovanillic acid was dissolved in 350 ml of N,N-dimethylformamide, further 80 ml of, benzyl chloride and 90 g of potassium carbonate were added thereto, and was the resultant mixture was stirred for 24 hours at 60° C. Thereafter, 30 ml of benzylchloride was added, and the resultant mixture was stirred for additional 15 hours at the same temperature. After cooling, 200 ml of triethylamine was added to the resultant solution and stirred for 30 minutes. The reaction mixture was poured into 150 ml of water and extracted with 300 ml of ethyl acetate three times. An organic layer was washed with 100 ml of water three times and 100 ml of 2N hydrochloric acid three times and 100 ml of water three times in this order. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from dichloromethane-ether, affording 98.3 g of 3-benzyloxy4-methoxybenzyl benzoate (93.0% yield). Physicochemical properties of the compound are as follows:

Workup

  1. temperatureAfter cooling
  2. stirringstirred for 30 minutes
  3. extractionextracted with 300 ml of ethyl acetate three times
  4. washAn organic layer was washed with 100 ml of water three times and 100 ml of 2N hydrochloric acid three times and 100 ml of water three times in this order
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-69dfcd57383f43cdbe7fa0fea279b095
Source dataset
uspto-grants-1997_05
Patent number
US05629340

Reaction notes

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