Benzyl Alcohol → Benzyl 2-cyclopentylacetate

HRID 516873Notes

Reaction equation

HRID 516873 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH:13]1([CH2:18][C:19]([OH:21])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)C1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH:13]1([CH2:18][C:19]([O:21][CH2:12][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 71606Cyclopentylacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 53419194Benzyl 2-cyclopentylacetateYield 703%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluene sulfonic acid monohydrate (1.48 g, 7.82 mmol) was added to a solution of cyclopentylacetic acid (10.0 g, 78.2 mmol) and benzyl alcohol (8.42 g, 78.2 mmol) in toluene (100 ml) at room temperature, a Dean-Stark water separator was mounted, and the mixture was refluxed for 4 hr. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure, the residue was dissolved in ether, the solution was washed with saturated sodium bicarbonate and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=97:3) to give the title compound as a light yellow oil (12.0 g, yield 70%).

Workup

  1. temperaturethe mixture was refluxed for 4 hr
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washthe solution was washed with saturated sodium bicarbonate and saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=97:3)

Sources & evidence

ORD record
ord-c47b2245bb0e4263b8c4fdaba489d0b1
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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