Hydrochloric Acid → 4-Methoxybicyclo(2.2.2)octane-1-carboxylic acid

HRID 2280829Notes

Reaction equation

HRID 2280829 reaction equation
[CH3:1][O:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]([O:13]C)=[O:12])([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.Cl>[OH-].[Na+]>[CH3:1][O:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]([OH:13])=[O:12])([CH2:5][CH2:4]1)[CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12765154Methyl 4-methoxybicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 127651534-Methoxybicyclo(2.2.2)octane-1-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-methoxybicyclo[2.2.2]octane-1-carboxylate (6.5 g, 33 mmol) was refluxed in aqueous sodium hydroxide solution (5%, 150 mL) for 2 h. After cooling down, the reaction solution was acidified with hydrochloric acid solution (6 N, 50 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were dried over magnesium sulfate and concentrated to afford the title compound (5.9 g, 32 mmol, yield 97%) which was used in the next step without further purification. MS (ESI) m/z=183.2 [M+H]−.

Workup

  1. temperatureAfter cooling down
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05a9d595841344fcb9ff585309138733
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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