Benzyl 4-Hydroxybenzoate → HCID 13878961, compound

HRID 2309561Notes

Reaction equation

HRID 2309561 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[CH:34]=[CH:33][CH:32]=[C:28]([C:29](Cl)=[O:30])[CH:27]=1>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[CH:34]=[CH:33][CH:32]=[C:28]([C:29]([O:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][C:24]4[CH:23]=[CH:15][CH:10]=[CH:11][CH:12]=4)=[O:7])=[CH:16][CH:17]=3)=[O:30])[CH:27]=2)=[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 7180Benzyl 4-HydroxybenzoateHCID 7451Isophthaloyl chlorideHCID 8471Triethylamine

Product 1

HCID 13878961HCID 13878961, 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 suspension of 25 g of isophthalic 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. Thereafter, the resulting reaction product is collected by filtration to obtain white crystals. The crystalline product is washed with 1500 ml of water twice and then with 1000 ml of methanol twice and subsequently, recrystallized from a mixture solvent of hexane-chloroform (1:1) to give di(p-benzyloxycarbonylphenyl)isophthalate melting at 105°-107° C. as white crystals.

Workup

  1. customInto a 500 ml four-neck flask equipped with a condenser tube
  2. additionis added dropwise
  3. temperaturewhile maintaining the mixture at 0°-3° C. over 3 hours
  4. additionAfter addition
  5. customto react at 0°-3° C. for 1 hour
  6. customThereafter, the resulting reaction product
  7. filtrationis collected by filtration
  8. customto obtain white crystals
  9. washThe crystalline product is washed with 1500 ml of water twice
  10. customwith 1000 ml of methanol twice and subsequently, recrystallized from a mixture solvent of hexane-chloroform (1:1)

Sources & evidence

ORD record
ord-28542f94e7884e4fb773dc42c81f1a9e
Source dataset
uspto-grants-1987_09
Patent number
US04695649

Reaction notes

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