Benzyl 4-Hydroxybenzoate → HCID 13587738, compound

HRID 1249107Notes

Reaction equation

HRID 1249107 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

A 500 ml. four-necked flask equipped with a condenser tube and a thermometer are charged with 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 over 3 hours with stirring while maintaining the mixture at 0°-5° C. After the addition, the mixture is further allowed to react at 0°-5° C. for hour. Therefore the reaction product is collected by filtration to obtain while crystals. The crystals are washed twice with 1500 ml of water and then twice with 1000 ml of methanol and subsequently, recrystallized from chloroform to give di(p-benzyloxycarbonylphenyl)terephthalate melting at 186°-187° C. as white crystals.

Workup

  1. customfour-necked flask equipped with a condenser tube
  2. additionis added dropwise over 3 hours
  3. temperaturewhile maintaining the mixture at 0°-5° C
  4. additionAfter the addition
  5. customto react at 0°-5° C. for hour
  6. filtrationTherefore the reaction product is collected by filtration
  7. customto obtain while crystals
  8. washThe crystals are washed twice with 1500 ml of water
  9. customtwice with 1000 ml of methanol and subsequently, recrystallized from chloroform

Sources & evidence

ORD record
ord-24c02144f0b640a3b34413db53d00109
Source dataset
uspto-grants-1986_12
Patent number
US04628336

Reaction notes

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