Isopropanol → 2-(2-Methoxyphenyl)cyclopentan-1-one

HRID 475863Notes

Reaction equation

HRID 475863 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[OH:14].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 12333721HCID 12333721, compoundHCID 131709961Jones' reagent

Product 1

HCID 123337222-(2-Methoxyphenyl)cyclopentan-1-oneYield 73.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(2-methoxyphenyl)cyclopentanol (9.11 g, 47.4 mmol) in Acetone (Volume: 474 ml) was added Jones reagent (6.52 ml, 52.1 mmol) (8.0 M). After the addition was complete (the conversion of red reagent to green solid, and the supernatant solution took on the color of unreacted reagent), isopropanol was added to quench the excess reagent. The green solid was filtered off through ceilite and rinsed with acetone. The filtrate was concentrated and purified by flash chromatography to get 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol, 73.6% yield). LC-MS (M+H)+=191.0. 1H NMR (500 MHz, CD3OD) δ 7.24 (td, J=7.8, 1.8 Hz, 1H), 7.09 (dd, J=7.5, 1.7 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.90 (td, J=7.4, 1.1 Hz, 1H), 3.77 (s, 3H), 3.43-3.37 (m, 1H), 2.48-2.30 (m, 3H), 2.23-2.11 (m, 2H), 2.00-1.88 (m, 1H).

Workup

  1. additionAfter the addition
  2. additionwas added
  3. customto quench the excess reagent
  4. filtrationThe green solid was filtered off through ceilite
  5. washrinsed with acetone
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9d0aa32e73f24259beef781e4627c39e
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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