Ammonium thiocyanate → 2,3,6-Trimethyl-4-thiocyanato-phenol

HRID 48195

反応式

HRID 48195 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[S-:11][C:12]#[N:13].[NH4+]>CO>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([OH:10])[C:4]([CH3:9])=[CH:5][C:6]=1[S:11][C:12]#[N:13]

参加物

4

反応物 2

HCID 15666Ammonium thiocyanateHCID 170162,3,6-Trimethylphenol

生成物 1

HCID 235038182,3,6-Trimethyl-4-thiocyanato-phenol収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

2,3,6-trimethylphenol (1.6 g, 11.8 mmol) was disolved in 50 mL of anhydrous methanol which had been deoxygenated by bubbling with nitrogen. Ammonium thiocyanate (2.2 g, 28,9 mmol) was added to this solution which was then cooled to 0° C. and bubbled with chlorine gas. The initially colorless homogeneous solution becomes pink and then green with the formation of a white precipitate. The solution was stirred for 1 h at 0° C. and then for a further hour at 20° C. The dissolved chlorine was removed by bubbling with nitrogen and the precipitate removed by filtration. Evaporation of the filtrate under reduced pressure followed by drying under high vacuum (0.1 torr) yielded 2.20 g (97%) of 2,3,5-Trimethyl-4-hydroxyphenylthiocyanate in a form pure enough for the next step in the synthesis. An analytical sample was recrystallized from hexanes: white crystals, mp 100.3° C. 1H NMR (CDCl3) δ 7.2 (s, 1H), 5.0 (s, 1H) 2.4 (s, 3H), 2.2 (s, 6H).

後処理

  1. customhad been deoxygenated
  2. customby bubbling with nitrogen
  3. custombubbled with chlorine gas
  4. waitfor a further hour at 20° C
  5. customThe dissolved chlorine was removed
  6. customby bubbling with nitrogen
  7. customthe precipitate removed by filtration
  8. customEvaporation of the filtrate under reduced pressure
  9. customby drying under high vacuum (0.1 torr)

出典と根拠

ORDレコード
ord-11afc3fb35574f929d544bc343c86946
出典データセット
uspto-grants-2004_03
特許番号
US06703384B2

関連ノート

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