Sulfuric Acid → Phenol, 4-(5-octyl-2-pyridinyl)-

HRID 1198834ノート

反応式

HRID 1198834 の反応式
S(=O)(=O)(O)O.[CH2:6]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:26]=[CH:25][C:23](N)=[CH:22][CH:21]=2)=[N:18][CH:19]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].N([O-])=[O:28].[Na+].[OH-].[Na+]>O>[CH2:6]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:26]=[CH:25][C:23]([OH:28])=[CH:22][CH:21]=2)=[N:18][CH:19]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19867286HCID 19867286、化合物HCID 23668193Sodium Nitrite

生成物 1

HCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-収率 35.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
5 °C

実験手順

10 ml of 3N sulphuric acid were treated while stirring with 1.8 g of p-(5-octyl-2-pyridyl)aniline. The mixture was cooled to 5° C. and then treated dropwise at 0°-5° C. within about 3 minutes with a solution of 0.442 g of sodium nitrite in 2 ml of water. The brown mixture obtained was poured into 100 ml of water and heated to reflux for 30 minutes while stirring. The reaction mixture was subsequently cooled to room temperature, adjusted to about pH 5 with 7 ml of 3N sodium hydroxide solution and extracted once with 200 ml of methylene chloride and once with 100 ml of methylene chloride. The organic phases were washed with 150 ml of dilute sodium chloride solution, dried over sodium sulphate and evaporated in a vacuum. The residue (1.867 g) was separated by chromatography on 250 g of silica gel at 0.4 bar with methylene chloride and methylene chloride/acetone. Recrystallization of the resulting red-brown oil in diethyl ether/hexane at 0° C. gave 0.635 g of p-(5-octyl-2-pyridyl)phenol as beige crystals. Working-up of the mother liquor gave 0.355 g of crude p-(5-octyl-2-pyridyl)phenol as a brown oil.

後処理

  1. customThe brown mixture obtained
  2. temperatureheated
  3. temperatureto reflux for 30 minutes
  4. temperatureThe reaction mixture was subsequently cooled to room temperature
  5. extractionextracted once with 200 ml of methylene chloride and once with 100 ml of methylene chloride
  6. washThe organic phases were washed with 150 ml of dilute sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated in a vacuum
  9. customThe residue (1.867 g) was separated by chromatography on 250 g of silica gel at 0.4 bar with methylene chloride and methylene chloride/acetone
  10. customRecrystallization of the resulting red-brown oil in diethyl ether/hexane at 0° C.

出典と根拠

ORDレコード
ord-160964ccfb6147fd93e64d94f8c58491
出典データセット
uspto-grants-1990_02
特許番号
US04898455

反応ノート

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