Benzoyl chloride → 3-Hydroxycyclopentyl benzoate

HRID 1934669Notes

Reaction equation

HRID 1934669 reaction equation
[CH:1]1([OH:7])[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:8]([O:6][CH:3]1[CH2:4][CH2:5][CH:1]([OH:7])[CH2:2]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 100165Cyclopentane-1,3-diol

Product 1

HCID 224676173-Hydroxycyclopentyl benzoateYield 62.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1,3-cyclopentanediol (500 mg) in pyridine (10 mL) was added benzoyl chloride (688 mg), and the mixture was stirred for 18 hours at ambient temperature. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water. The separated organic layer was washed with 1N-hydrochloric acid, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (3:1 to 1:1) to give 3-hydroxycyclopentyl benzoate as a colorless oil (630 mg).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with 1N-hydrochloric acid, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by a silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (3:1 to 1:1)

Sources & evidence

ORD record
ord-f2ca7cf947044ce880e8861396c294d2
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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