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

HRID 1271624노트

반응식

HRID 1271624 반응식
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)(=[O:3])[CH3:2].[OH-:14].[Na+].[Mn]([O-])(=O)(=O)=[O:17].[K+].[OH2:22]>>[OH:14][C:6]12[CH2:12][CH:10]3[CH2:9][CH:8]([CH2:13][C:4]([C:1](=[O:3])[C:2]([OH:17])=[O:22])([CH2:11]3)[CH2:5]1)[CH2:7]2

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

30 g of 1-acetyladamantane was added to solution of 6.8 g of NaOH in 500 mL of water. The temperature of the suspension was increased to 40–50° C. and 80 g of potassium permanganate was added during a period of 1.5 h. The obtained mixture was stirred at 50–55° C. for 6 h and thereafter at room temperature 27° C. for 17 h followed by separation of the formed manganese dioxide precipitate by means of filtration. After the filtrate work-up that included acidification of filtrate, extractions with organic solvent and concentration of the combined organic phases, 28 g of partly crystallized material was obtained. Recrystallization of the material gave 13.6 g of the target 3-hydroxyadamantaneglyoxylic acid (1) as white crystalline solid with the purity 92.1% according to GC analysis of the corresponding methyl ester.

후처리

  1. temperatureThe temperature of the suspension was increased to 40–50° C.
  2. customat room temperature 27° C. for 17 h followed by separation of the formed manganese dioxide precipitate by means of filtration
  3. extractionacidification of filtrate, extractions with organic solvent and concentration of the combined organic phases, 28 g of partly crystallized material
  4. customwas obtained
  5. customRecrystallization of the material

출처 및 근거

ORD 기록
ord-0a0332dcef9e44868356d319dce5ede5
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205432B2

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