Methyl 4-oxoadamantane-1-carboxylate → 4-Oxoadamantane-1-carboxylic acid

HRID 38451

Reaction equation

HRID 38451 reaction equation
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([C:8]3=[O:15])[CH2:6]1)[CH2:12]2)=[O:4]>[Li+].[OH-].CO>[O:15]=[C:8]1[CH:9]2[CH2:14][C:5]3([C:3]([OH:4])=[O:2])[CH2:12][CH:11]([CH2:13][CH:7]1[CH2:6]3)[CH2:10]2

Participants

3

Reactant 1

HCID 4078246Methyl 4-oxoadamantane-1-carboxylate

Product 1

HCID 28425154-Oxoadamantane-1-carboxylic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 23717829Lithium hydroxide methanolSolvent2×

Procedure

1.64 g of 4-Oxo-adamantane-1-carboxylic acid methyl ester (10) were dissolved in 4 mL of 2M aq. LiOH/MeOH (1:1) and stirred overnight at room temperature. Additional 5 ml of the MeOH/LiOH mixture were added and stirring was continued until conversion was complete. The reaction mixture was acidified and extracted three times with ethyl acetate. The organic layer was dried over sodium sulphate and evaporated to dryness to give 1.4 g of (11) as a solid. Rt=0.87 min (Method 3). Detected mass: 195.2 (M+H+).

Workup

  1. stirringstirring
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b7ee97e955b94020b86d383c0be4c984
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Linked notes

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