Water → Benzoic acid cyclopent-3-enylmethyl ester

HRID 1734632Notes

Reaction equation

HRID 1734632 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH:6]=[CH:5][CH2:4]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>N1C=CC=CC=1>[CH:3]1([CH2:2][O:1][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 1514122Cyclopent-3-en-1-ylmethanol

Product 1

HCID 10241948Benzoic acid cyclopent-3-enylmethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, cooled (0° C.) solution of 4-hydroxymethylcyclopentene (J. -P. Depres and A. E. Green, J. Org. Chem. 1984, 49, 928-931, and references therein) (37.0 g, 276 mmol) in pyridine (450 mL) was added benzoylchloride (32.1 mL, 276 mmol) over 30 minutes. The resulting mixture was stirred at room temperature for 1.25 hours. Water (50 mL) was added and the volatiles removed in vacuo. The residual oil was dissolved in chloroform and the solution extracted with water and then dried over sodium sulfate. Evaporation of solvent gave (3-cyclopenten-1-yl)methylbenzoate as a yellow oil (53.94 g, 91%), sufficiently pure for use; 1H-NMR (DMSO-d6)δ: 7.98, 7.67, 7.56 (m, 5, C6H5), 5.72 (s, 2, CH=CH), 4.19 (m, 2, OCH2), 2.71 (m, 1, CH), 2.56-2.77 (m, overlapping solvent, 2CH), 2.21-2.14 (m, 2, 2CH).

Workup

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residual oil was dissolved in chloroform
  3. extractionthe solution extracted with water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-652526e3993f48438517df6914d0d289
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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