Benzyl Alcohol → Benzyl 2-cyclopentylacetate

HRID 977642Notes

Reaction equation

HRID 977642 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 90.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of cyclopentylacetic acid (10.02 g, 78.2 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 2h. 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; 1H NMR (300 MHz, CDCl3)δ: 7.35(m, 5H), 5.10(s, 2H), 2.40(d, j=8 Hz, 2H), 2.26(m, 1H), 1.81 (m, 2H), 1.6 (m, 4H), 1.18(m, 2H).

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-2e73c6f8223d42c785d4b569c75c15b6
Source dataset
uspto-grants-1997_03
Patent number
US05614649

Reaction notes

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