Water → 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid

HRID 1271626Notes

Reaction equation

HRID 1271626 reaction equation
[OH-:1].[Na+].[C:3]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2)(=[O:5])[CH3:4].[Mn]([O-])(=O)(=O)=[O:17].[K+].[OH2:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][C:8]12[CH2:14][CH:12]3[CH2:11][CH:10]([CH2:15][C:6]([C:3](=[O:5])[C:4]([OH:17])=[O:22])([CH2:13]3)[CH2:7]1)[CH2:9]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketoneHCID 516875Potassium Permanganate

Product 1

HCID 104661932-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
50 °C

Procedure

3.0 mL of NaOH 30% solutions in water was diluted with 120 mL of water. The solution was heated to 50° C. and 0.36 g of tetrabutylammonium bromide was added to the solution. Now 10 g of 1-acetyladamantane was added while stirring, followed by addition of 24.8 g of potassium permanganate during 4 h at 50–52° C. Stirring was continued for additional 4 h. The mixture was allowed to stay at room temperature for overnight and then manganese dioxide precipitate was filtered out. The filtrate work-up included acidification of filtrate, extraction and partial concentration of the combined organic phase. To the concentrated solution 10 mL of organic solvent was added and the mixture was kept at room temperature overnight. The formed crystals were filtered out, washed with solvent and dried to yield 4.7 g of the target 3-hydroxyadamantaneglyoxylic acid (1) with purity 96.4% according to GC analysis of the corresponding methyl ester.

Workup

  1. stirringStirring
  2. waitto stay at room temperature for overnight
  3. filtrationmanganese dioxide precipitate was filtered out
  4. extractionacidification of filtrate, extraction and partial concentration of the combined organic phase
  5. additionTo the concentrated solution 10 mL of organic solvent was added
  6. waitthe mixture was kept at room temperature overnight
  7. filtrationThe formed crystals were filtered out
  8. washwashed with solvent
  9. customdried

Sources & evidence

ORD record
ord-1ca49c610a9b41ee97214286b1d99151
Source dataset
uspto-grants-2007_04
Patent number
US07205432B2

Reaction notes

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