Ethyl 2-(benzyloxymethyl)cyclopropanecarboxylate → 2-((Benzyloxy)methyl)cyclopropanecarboxylic acid

HRID 496052Notes

Reaction equation

HRID 496052 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[C:13]([O:15]CC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+].CS(C)=O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 22325150Ethyl 2-(benzyloxymethyl)cyclopropanecarboxylate

Product 1

HCID 223251512-((Benzyloxy)methyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.23 mol of the compound obtained in Step 1 in 500 ml of ethanol, 230 ml of 1N sodium hydroxide solution and 5 ml of dimethyl sulphoxide is heated at reflux for 2 hours and is then concentrated. The residue is taken up in a mixture of water/ether. After conventional treatment, the combined organic phases are concentrated. Chromatography of the residue over silica gel (dichloromethane/tetrahydrofuran: 97/3) allows a cis/trans mixture of the products obtained to be isolated, some of the fractions of which have a preponderance of the cis isomer and some a preponderance of the trans isomer.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationis then concentrated
  3. additionThe residue is taken up in a mixture of water/ether
  4. concentrationAfter conventional treatment, the combined organic phases are concentrated
  5. additiona cis/trans mixture of the products
  6. customobtained
  7. customto be isolated

Sources & evidence

ORD record
ord-e57c419485054918975b09e35f212ebe
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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