Pyridine → 1,4-Xylenediol dibenzoate

HRID 132712Notes

Reaction equation

HRID 132712 reaction equation
[C:1]1([CH3:10])[C:2]([OH:9])=[C:3]([OH:8])[C:4]([CH3:7])=[CH:5][CH:6]=1.N1C=C[CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[C:17]([O:8][C:3]1[C:4]([CH3:7])=[CH:5][CH:6]=[C:1]([CH3:10])[C:2]=1[O:9][C:30](=[O:26])[C:29]1[CH:14]=[CH:13][CH:12]=[CH:27][CH:28]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 114691143,6-Dimethylbenzene-1,2-diol

Product 1

HCID 593975851,4-Xylenediol dibenzoateYield 95%

Procedure

To 0.03 mol 1,4-xylenediol were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by recrystallization from ethyl acetate and petroleum ether (1:1, v/v) to give 1,4-xylenediol dibenzoate as a white solid, and the yield was 95%, mp was 84-85° C. 1HNMR: δ (ppm) 5.3(4H, s, CH2 linked to ester radical), 7.4-8.1(10H, m, ArH)

Workup

  1. temperatureThe reaction was heated
  2. temperaturerefluxing for 4 hours
  3. temperaturecooled
  4. additionadded 20 ml saturated saline
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customAfter removing solvent
  9. customthe crude was purified by recrystallization from ethyl acetate and petroleum ether (1:1

Sources & evidence

ORD record
ord-a558f7840ab64592ba839371c68b3ff6
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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