Pyridine → Benzoic acid cyclopent-3-enylmethyl ester

HRID 19422Notes

Reaction equation

HRID 19422 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.N1C=CC=CC=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH:1]1([CH2:6][O:7][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 1514122Cyclopent-3-en-1-ylmethanol

Product 1

HCID 10241948Benzoic acid cyclopent-3-enylmethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

In a flask under argon was placed cyclopent-3-enyl-methanol (7.86 g, 80 mmol) and pyridine (100 mL). To this mixture was slowly added benzoyl chloride (9.30 mL, 80 mmol). After addition was complete, the mixture was stirred at 25° C. for 1.5 h. After this time, the mixture was slowly treated with water (15 mL) and concentrated in vacuo to remove most of the pyridine. The mixture was taken up into chloroform (400 mL) and washed with water (300 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford benzoic acid cyclopent-3-enylmethyl ester (15.86 g, 98%) as a light yellow oil.

Workup

  1. customIn a flask under argon was placed
  2. additionAfter addition
  3. concentrationconcentrated in vacuo
  4. customto remove most of the pyridine
  5. washwashed with water (300 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b42887b703bc478aae0d00880ef37b51
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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