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

HRID 1271625Notes

Reaction equation

HRID 1271625 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]>>[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

5

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

Procedure

1.7 mL of NaOH 30% solution in water was diluted with 500 mL of water and 60 g of 1-acetyladamantane was added to that solution. Temperature of the suspension was increased to 35–40° C. and 144 g of potassium permanganate was added to the suspension during 0.5 h. The mixture was stirred at 35–40° C. for 25 h followed by manganese dioxide precipitate filtration. The filtrate work-up procedure consisting of acidification, extractions with organic solvent and concentration of the combined organic phases which resulted in 25.2 g of the target 3-hydroxyadamantaneglyoxylic acid (1) with purity 85.7% according to GC analysis of the corresponding methyl ester.

Workup

  1. additionwas added to that solution
  2. temperatureTemperature of the suspension was increased to 35–40° C.
  3. filtrationfollowed by manganese dioxide precipitate filtration
  4. extractionThe filtrate work-up procedure consisting of acidification, extractions with organic solvent and concentration of the combined organic phases which

Sources & evidence

ORD record
ord-57c72cc5f60e41d58764620c4674ce2b
Source dataset
uspto-grants-2007_04
Patent number
US07205432B2

Reaction notes

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