Sodium Hydroxide → HCID 86665070, compound

HRID 333345Notes

Reaction equation

HRID 333345 reaction equation
[Cl:1][C:2](=[CH2:13])[CH2:3][C:4]1([C:9]([O:11]C)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1.[OH-].[Na+]>CO>[Cl:1][C:2](=[CH2:13])[CH2:3][C:4]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86665069HCID 86665069, compound

Product 1

HCID 86665070HCID 86665070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(2-chloroallyl)cyclopentanecarboxylate (1.82 g, 8.98 mmol) in MeOH (30 mL) was added 1M NaOH (26.9 mL, 26.9 mmol) at room temperature. The mixture was stirred at room temperature for 2 hour then heated at 60° C. for 24 hours. The reaction mixture was quenched with excess of aq. 1 M HCl. The mixture was extracted with EtOAc, and the organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash chromatography using 30% EtOAc/heptane to 100% EtOAc to give 1-(2-chloroallyl)cyclopentanecarboxylic acid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43-1.82 (m, 6H), 2.04-2.28 (m, 2H), 2.69 (s, 2H), 5.08 (s, 1H), 5.17 (d, J=1.0 Hz, 1H).

Workup

  1. temperaturethen heated at 60° C. for 24 hours
  2. customThe reaction mixture was quenched with excess of aq. 1 M HCl
  3. extractionThe mixture was extracted with EtOAc
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-afcb4ef2997b4b028cabd2d5df056b14
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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