Benzyl Alcohol → Benzyl 2-cyclopentylacetate

HRID 1079049Notes

Reaction equation

HRID 1079049 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH:1]1([CH2:6][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

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

Product 1

HCID 53419194Benzyl 2-cyclopentylacetateYield 860.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of cyclopentylacetic acid (10.02 g, 8.2 mmol), benzyl alcohol (8.45 g, 78.2 mmol) and p-toluenesulfonic acid monohydrate (1.48 g, 7.82 mmol) in benzene (60 mL) was refluxed using a Dean-Stark water separator for 2 h. After cooling, benzene was removed and the mixture was diluted with ether (50 mL) and washed successively with saturated NaHCO3 solution, saturated brine solution, dried and evaporated to give the compound (15.40 g) as an oil;

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. custombenzene was removed
  4. additionthe mixture was diluted with ether (50 mL)
  5. washwashed successively with saturated NaHCO3 solution, saturated brine solution
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-39321a0bd2224d0d9df3d44a207cf4bd
Source dataset
uspto-grants-1996_08
Patent number
US05550262

Reaction notes

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