Hydrochloric Acid → 1-Carboxymethyl-cyclopentanecarboxylic acid benzyl ester

HRID 1469658Notes

Reaction equation

HRID 1469658 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([CH2:16][CH:17]=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:19].[Na+].Cl>C1COCC1.[Ag]=O>[CH2:1]([O:8][C:9]([C:11]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86648214HCID 86648214, compound

Product 1

HCID 216902921-Carboxymethyl-cyclopentanecarboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Next, to a solution of 1-(2-oxo-ethyl)-cyclopentanecarboxylic acid benzyl ester (200 mg, 0.81 mmol) in THF (5 mL) is added silver(II) oxide (201 mg, 1.62 mmol) and aqueous 1M NaOH (0.81 mL of 1.0 N, 0.81 mmol) and the suspension is stirred at room temperature for 18 hours. The mixture is acidified to pH 3 with aqueous 1M HCl and is extracted with ethyl acetate. The organic layer is washed with water, brine, dried over MgSO4 and filtered. The solvent is removed under reduced pressure to furnish 1-carboxymethyl-cyclopentanecarboxylic acid benzyl ester MS 263.3 (M+1).

Workup

  1. extractionis extracted with ethyl acetate
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c54d147e7bb14f738735090038b28feb
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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