Catechol → Spiro[1,3-benzodioxole-2,1′-cyclopentane]

HRID 1354772Notes

Reaction equation

HRID 1354772 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[C:9]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:9]12([O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=3[O:2]1)[CH2:13][CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 289CatecholHCID 6101p-Toluenesulfonic acidHCID 8452Cyclopentanone

Product 1

HCID 12608169Spiro[1,3-benzodioxole-2,1′-cyclopentane]

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Catechol (11 g) and cyclopentanone (9 ml) were heated under reflux in toluene (150 ml) with p-toluenesulfonic acid (0.18 g) with a water trap. After 18 hours, the mixture was concentrated and purified by chromatography (silica gel, heptane/ethyl acetate 4:1). This resulted in the product with the molecular weight of 176.22 (C11H12O2); MS(ESI): 177 (M+H+).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by chromatography (silica gel, heptane/ethyl acetate 4:1)
  3. customThis resulted in the product with the molecular weight of 176.22 (C11H12O2)

Sources & evidence

ORD record
ord-289e1de8b3384f3fb86d5f070da8e726
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

Loading…