Sodium Hydroxide → 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid

HRID 1271627Notes

Reaction equation

HRID 1271627 reaction equation
[OH-].[Na+].[C:3]12([C:13](=[O:17])[C:14]([OH:16])=[O:15])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[Mn]([O-])(=O)(=O)=[O:19].[K+]>O>[OH:19][C:9]12[CH2:11][CH:5]3[CH2:6][CH:7]([CH2:12][C:3]([C:13](=[O:17])[C:14]([OH:16])=[O:15])([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 13734294α-Oxotricyclo[3.3.1.13,7]decane-1-acetic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
55 °C

Procedure

2.8 mL of NaOH 30% solution in water was diluted with 30 mL of water. The solution was heated to 55° C. and 3.0 g of adamantaneglyoxylic acid was dissolved therein. Then 3.3 g of potassium permanganate was added gradually during 2 h and stirring of obtained the obtained mixture was continued for 9 h at 55–60° C. The mixture was allowed to stay at room temperature for overnight. Then manganese dioxide precipitate was filtered out and the filtrate work-up procedure consisting of acidification, extraction with organic solvent and concentration of the combined organic phases resulted in 2.5 g of the target 3-hydroxyadamantaneglyoxylic acid (1) with purity 68.9% according to GC analysis of the corresponding methyl ester.

Workup

  1. customof obtained the obtained mixture
  2. waitto stay at room temperature for overnight
  3. filtrationThen manganese dioxide precipitate was filtered out
  4. extractionthe filtrate work-up procedure consisting of acidification, extraction with organic solvent and concentration of the combined organic phases

Sources & evidence

ORD record
ord-0cd32d9d9ed5429783e4274235b59d06
Source dataset
uspto-grants-2007_04
Patent number
US07205432B2

Reaction notes

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