p-Toluenesulfonic acid → 3-(2-Hydroxyethyl)cyclopentan-1-one

HRID 1093096Notes

Reaction equation

HRID 1093096 reaction equation
C[O:2][C:3]1(OC)[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][OH:10])[CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[OH:10][CH2:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:3](=[O:2])[CH2:4]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 534035542-(3,3-Dimethoxycyclopentyl)ethanol

Product 1

HCID 128928653-(2-Hydroxyethyl)cyclopentan-1-oneYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-(3,3-dimethoxycyclopentyl)ethanol (203.3 g, 1167 mmol), in Et2O (1000 mL) was treated with p-toluene sulfonic acid (6.66 g, 35.0 mmol) and stirred for 16 hrs. The solution was extracted with water (4×100 mL) and the combined extracts were concentrated under reduced pressure to give the title compound (142.33 g, 1110 mmol, 95% yield), as a dark brown oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.64-3.76 (2 H, m), 2.41 (1 H, dd, J=17.85, 7.17 Hz), 2.24-2.35 (2 H, m), 2.13-2.23 (2 H, m), 1.82 (1 H, dd, J=18.01, 10.38 Hz), 1.64-1.77 (2 H, m), 1.49-1.60 (1 H, m). 13C NMR (126 MHz, CDCl3) δ ppm 219.75, 61.30, 45.21, 38.54, 38.41, 34.01, 29.67.

Workup

  1. extractionThe solution was extracted with water (4×100 mL)
  2. concentrationthe combined extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-30e1a7535fe74a668007be748aa0135f
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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