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Benzyl Alcohol → 2-(Benzyloxy)pyridine-4-carboxylic acid

HRID 333812
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HRID 333812 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[K])(C)(C)C.O>CN1C(=O)CCC1>[CH2:11]([O:18][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 2369852-Chloroisonicotinic acidHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 229262722-(Benzyloxy)pyridine-4-carboxylic acid수율 71.3%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
125 °C

실험 절차

2-Chloro isonicotinic acid (9.45 g) and benzyl alcohol (12.977 g) were dissolved in NMP (180 mL), and treated with tBuOK (20.2 g) between 10-25° C. The reaction mixture was then stirred at 125° C. (Bath-temperature) for 6 h, cooled down to r.t., poured into water (1500 ml) and extracted twice with water. The combined aqueous phases were treated with concentrated aqueous HCl until pH 3 (16 ml). After 10 min the solid was filtered, washed with water and dried under high vacuum, to give the title compound as an off-white solid (9.8 g). MS (m/e)=228.1 (M−H).

후처리

  1. temperaturecooled down to r.t.
  2. extractionextracted twice with water
  3. additionThe combined aqueous phases were treated with concentrated aqueous HCl until pH 3 (16 ml)
  4. filtrationAfter 10 min the solid was filtered
  5. washwashed with water
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-82ae8e39b44a4d4682ea5910c4ad8050
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08883786B2

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