Hydrochloric Acid → Cyclopentanecarboxylic acid, 2,2,5,5-tetramethyl-

HRID 986866Notes

Reaction equation

HRID 986866 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[C:9](N)=[O:10].[OH-:13].[Na+].Cl>CO>[CH3:1][C:2]1([CH3:12])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[C:9]([OH:13])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14028850(2,2,5,5-Tetramethylcyclopentane-1-yl)carboxamide

Product 1

HCID 10197889Cyclopentanecarboxylic acid, 2,2,5,5-tetramethyl-Yield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

3.38 g of (2,2,5,5-tetramethylcyclopentane-1-yl)carboxamide was dissolved in 30 ml of methanol, and 15 ml of an aqueous 3N sodium hydroxide solution was added thereto. Then, the mixture was heated at 80° C. for 5 hours. After cooling, 40 ml of 2N hydrochloric acid was added thereto, and the mixture was extracted with 100 ml and 50 ml of ethyl acetate. The organic layers were combined, washed with 100 ml of water and 50 ml of aqueous saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure, whereby 3.20 g of 2,2,5,5-tetramethylcyclopentanecarboxylic acid was obtained. Yield 94%. (m.p. 113.6° C.)

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with 100 ml and 50 ml of ethyl acetate
  3. washwashed with 100 ml of water and 50 ml of aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of magnesium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3aee1e8a2c78429486a345b7c8d19956
Source dataset
uspto-grants-1987_12
Patent number
US04716241

Reaction notes

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