Hydrochloric Acid → 6-Oxobicyclo[2.2.1]heptane-2-carboxylic acid

HRID 527086

Reaction equation

HRID 527086 reaction equation
Br[CH:2]1[CH:6]2[O:7][C:8](=[O:11])[CH:9]3[CH2:10][CH:3]1[CH2:4][CH:5]23.[OH-:12].[Na+].Cl>O>[O:12]=[C:6]1[CH:5]2[CH2:4][CH:3]([CH2:10][CH:9]2[C:8]([OH:7])=[O:11])[CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2636406-Bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-one2×

Product 1

HCID 3619876-Oxobicyclo[2.2.1]heptane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one, 72a, (28.0 g, 129.0 mmol) was treated with NaOH (258.0 mL of 2 M solution, 516.0 mmol) in H2O (350 mL) for 2 hour at room temperature. The reaction mixture was acidified with conc. HCl, extracted with Et2O. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient) to provide 16 g of 6-oxonorbornane-2-carboxylic acid.

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-24e9934f5647439ca376bdd4d797d436
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Linked notes

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