Catechol → o-Phenylene dibenzoate

HRID 132708Notes

Reaction equation

HRID 132708 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[O:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.N1C=C[CH:17]=[CH:16][CH:15]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[C:13]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 289CatecholHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028Tetrahydrofuran

Product 1

HCID 69514o-Phenylene dibenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.5 g pyrocatechol were added 50 ml tetrahydrofuran and 12.1 ml pyridine with stirring. Then to the resulting homogeneous mixture was slowly added 14.5 ml benzoyl chloride, and the reaction was stirred at room temperature for 1 hour, then heated refluxing for 4 hours. Next, 70 ml water was added to dissolve the resulting salt. The reaction mixture was extracted with toluene. Organic phase was separated, washed with saturated saline for two times, dried over anhydrous sodium sulfate. Removing solvent gave a white solid. After recrystallizing from ethyl acetate, 1,2-phenylene dibenzoate was obtained as a white crystal, the yield was 94%, and m.p. was 75-77° C.

Workup

  1. stirringthe reaction was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 4 hours
  4. dissolutionto dissolve the resulting salt
  5. extractionThe reaction mixture was extracted with toluene
  6. customOrganic phase was separated
  7. washwashed with saturated saline for two times
  8. dry with materialdried over anhydrous sodium sulfate
  9. customRemoving solvent gave a white solid
  10. customAfter recrystallizing from ethyl acetate

Sources & evidence

ORD record
ord-0083c813f29248ca836499c60a0346a2
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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