Sodium Hydroxide → 4-(Pyridin-3-ylmethyl)phenol

HRID 1154707ノート

反応式

HRID 1154707 の反応式
N([O-])=O.[Na+].N[C:6]1[CH:18]=[CH:17][C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1.[OH-:19].[Na+]>O.S(=O)(=O)(O)O>[OH:19][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 103751334-(Pyridin-3-ylmethyl)anilineHCID 23668193Sodium Nitrite

生成物 1

HCID 132901354-(Pyridin-3-ylmethyl)phenol

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
160 °C

実験手順

A solution of sodium nitrite (0.350 g) in water (1.5 ml) is cooled in ice, and added, with stirring, to a cold (ice-bath) solution of 3-(4'-aminobenzyl)pyridine (Preparation 8, 0.920 g, 0.0050 mole) in water (3.75 ml), concentrated sulfuric acid (2.5 ml), and ice (7 g). This solution in turn is added dropwise to a third solution of water (5 ml) and sulfuric acid (6.25 ml) that is maintained at 160° C. in an oil bath. The resulting solution is kept at 160° C. for 10 min and then cooled to room temperature. The pH of the solution is adjusted to 7.0 by addition of aqueous 50% sodium hydroxide. The resulting mixture is extracted 4 times with 25 ml of ether. The aqueous portion is further extracted continuously with ether for 40 hr. The ether extracts are washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crystalline residue is decolorized with activated charcoal and is recrystallized from acetone-hexane, giving a first crop (0.426 g) of the titled crystals, with a melting point of 182°-185° C. A second crop (0.034 g) and third crop (0.050 g, total 0.510 g, 0.00276 mole, 55%) of titled crystals are also obtained. Recrystallization of the first crop from acetone-hexane gives the titled product as colorless crystals with a melting point of 184°-186° C. IR (nujol) peaks are observed at 2900, 2800, 2720, 2680, 2600, 1615, 1590, 1580, 1515, 1485, 1280, 1250, 845, 800, 710, and 640 cm-1.

後処理

  1. additionadded
  2. temperaturecooled to room temperature
  3. extractionThe resulting mixture is extracted 4 times with 25 ml of ether
  4. extractionThe aqueous portion is further extracted continuously with ether for 40 hr
  5. washThe ether extracts are washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customis recrystallized from acetone-hexane

出典と根拠

ORDレコード
ord-591947a5fd1a408ab89e1c06f6250889
出典データセット
uspto-grants-1984_12
特許番号
US04490531

反応ノート

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