Benzyl 4-Hydroxybenzoate → HCID 13587738, compound

HRID 2309560Notes

Reaction equation

HRID 2309560 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][C:29]([C:30](Cl)=[O:31])=[CH:28][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][C:29]([C:30]([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:31])=[CH:28][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 7488Terephthaloyl chlorideHCID 8471Triethylamine

Product 1

HCID 13587738HCID 13587738, 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 60 ml of toluene. A suspension of 25 g of terephthalic dichloride in 100 ml of toluene is added dropwise with stirring while retaining the mixture at 0°-5° C. over 3 hours. After addition, the mixture is further allowed to react at 0°-5° C. for 1 hour. Thereafter the resulting reaction product is collected by filtration to obtain white crystals. The crystals are washed with 1500 ml of water twice and then with 1000 ml of methanol twice and subsequently, recrystallized from chloroform to give di(p-benzyloxycarbonylphenyl)terephthalate melting at 186°-187° C. as white crystals.

Workup

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

Sources & evidence

ORD record
ord-16823c1004be48b0a5f4d116100a7a69
Source dataset
uspto-grants-1987_09
Patent number
US04695649

Reaction notes

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