Pyridine → 583036-30-0

HRID 132714Notes

Reaction equation

HRID 132714 reaction equation
[CH3:1][CH2:2][CH:3]([OH:9])[CH2:4][CH:5]([OH:8])[CH2:6][CH3:7].N1C=C[CH:13]=[CH:12][CH:11]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[C:16]([O:8][CH:5]([CH2:4][CH:3]([O:9][C:29](=[O:25])[C:28]1[CH:13]=[CH:12][CH:11]=[CH:26][CH:27]=1)[CH2:2][CH3:1])[CH2:6][CH3:7])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 126413673,5-Heptanediol

Product 1

HCID 23125870583036-30-0Yield 92%

Procedure

To 0.03 mol 3,5-heptandiol 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 column chromatography to give 3,5-heptandiol dibenzoate as a colorless viscous liquid, and the yield was 92%.

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 column chromatography

Sources & evidence

ORD record
ord-af631ffe230348e9bd1438b14b243f69
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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