Phthaloyl chloride → HCID 13878971, compound

HRID 2309562Notes

Reaction equation

HRID 2309562 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(N([CH2:23][CH3:24])CC)C.[C:25](Cl)(=[O:35])[C:26]1[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:28](Cl)=[O:29]>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:16]=[CH:17][C:2]([O:1][C:25](=[O:35])[C:26]2[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][C:24]3[CH:23]=[CH:15][CH:10]=[CH:11][CH:12]=3)=[O:7])=[CH:16][CH:17]=2)=[O:29])=[CH:3][CH:4]=1)=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6955Phthaloyl chlorideHCID 7180Benzyl 4-HydroxybenzoateHCID 8471Triethylamine

Product 1

HCID 13878971HCID 13878971, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a 500 ml four-neck flask equipped with a condenser tube and a thermometer are charged 56 g of benzyl p-hydroxybenzoate, 25 g of triethylamine and 160 ml of toluene. A solution of 25 g of phthalic dichloride in 100 ml of toluene is added dropwise with stirring while maintaining the mixture at 0°-3° C. over 3 hours. After addition, the mixture is further allowed to react at 0°-3° C. for 1 hour. Then the reaction product is filtered, the filtrate solution is washed with 500 ml of water twice and concentrated under diminished pressure to distill the toluene off, and thereafter, 100 ml of hexane is added to the solution with stirring to give white crystals. The product is recrystallized from a mixture solvent of hexane-ethyl acetate (1:1) to yield di(p-benzyloxycarbonylphenyl)phthalate melting at 100°-103° C. as white crystals.

Workup

  1. customInto a 500 ml four-neck flask equipped with a condenser tube
  2. temperaturewhile maintaining the mixture at 0°-3° C. over 3 hours
  3. additionAfter addition
  4. customto react at 0°-3° C. for 1 hour
  5. filtrationThen the reaction product is filtered
  6. washthe filtrate solution is washed with 500 ml of water twice
  7. concentrationconcentrated under diminished pressure
  8. distillationto distill the toluene off, and thereafter, 100 ml of hexane
  9. additionis added to the solution
  10. stirringwith stirring
  11. customto give white crystals
  12. customThe product is recrystallized from a mixture solvent of hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bb802e9e50b543fa9a348962da11c5a8
Source dataset
uspto-grants-1987_09
Patent number
US04695649

Reaction notes

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