Potassium Hydroxide → 5,6-Dihydro-4H-cyclopenta[c]furan-5-carboxylic acid
Reaction equation
[C:1]([CH:6]1[CH2:13][C:9]2=[CH:10][O:11][CH:12]=[C:8]2[CH2:7]1)([O:3]CC)=[O:2].[OH-].[K+]>C(O)C.O>[C:1]([CH:6]1[CH2:13][C:9]2=[CH:10][O:11][CH:12]=[C:8]2[CH2:7]1)([OH:3])=[O:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Dissolve 5-(carboethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan (6.2 g, 34.1 mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidify the aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan.
Workup
- customPartition between water (150 mL) and ethyl ether (2×150 mL)
- extractionExtract with methylene chloride (2×150 mL)
- dry with materialdry (Na2SO4)
- customevaporate the solvent in vacuo
Sources & evidence
- ORD record
- ord-4bb0c1db3f6846b1818ef47dfa80f52e
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05591739
Reaction notes
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