Formic Acid → 2-Adamantanecarboxylic acid

HRID 2054562

반응식

HRID 2054562 반응식
S(=O)(=O)(O)O.C(Cl)(Cl)(Cl)Cl.[CH:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH:12]1O)[CH2:18]2.[CH:22]([OH:24])=[O:23]>>[CH:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH:12]1[C:22]([OH:24])=[O:23])[CH2:18]2

참가 물질

5

반응물 4

HCID 284Formic AcidHCID 1118Sulfuric Acid2회HCID 5943Carbon TetrachlorideHCID 641492-Adamantanol

생성물 1

HCID 3038022-Adamantanecarboxylic acid수율 5%

반응 조건

온도
0 °C

실험 절차

Concentrated sulfuric acid (50 mL) and carbon tetrachloride (100 mL) were combined, cooled to 0° C. and vigorously stirred. Adamantan-2-ol (451 mg) was dissolved in 96% formic acid (6 mL) and the solution was added to the sulfuric acid over 1 hour. The reaction continued to stir at 0° C. for 90 min after which it was added to 300 mL of ice. The layers were separated and the aqueous layer was extracted with 50 mL carbon tetrachloride (2×). The organic layers were combined and extracted with 1N NaOH. The aqueous portion was extracted with methylene chloride (4×) then acidified with 5N HCl. The solution turned white and was cooled on ice. Filtration provided the desired adamantane-2-carboxylic acid (contaminated with about 5% adamantane-1-carboxylic acid) as a white powder.

후처리

  1. stirringto stir at 0° C. for 90 min after which it
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 50 mL carbon tetrachloride (2×)
  4. extractionextracted with 1N NaOH
  5. extractionThe aqueous portion was extracted with methylene chloride (4×)
  6. temperaturewas cooled on ice
  7. filtrationFiltration

출처 및 근거

ORD 기록
ord-683e1908698748e8ab56973f7301dcf7
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329683B2

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