Hydrochloric Acid → 2-Ethyl-6-methylphenol

HRID 491127

反応式

HRID 491127 の反応式
Cl.N([O-])=O.[Na+].[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1N)[CH3:7].[OH:16]S(O)(=O)=O>O.CCO>[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1[OH:16])[CH3:7]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 324852-Ethyl-6-methylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 5193332-Ethyl-6-methylphenol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
70 °C

実験手順

19.4 mL (0.23 mmol) concentrated HCl and a solution of 16.1 g (0.23 mmol) sodium nitrite in water (approx. 70 mL) were added to a solution of 30 g (222 mmol) 2-ethyl-6-methyl-aniline in 135 mL EtOH at 0° C. and the mixture was stirred for 15 min. This mixture was added at 45° C. to a solution of 10.5 mL concentrated H2SO4 in 300 mL water and at the end of the addition heated to 70° C. The aqueous phase was cooled to RT and exhaustively extracted with EtOAc. The combined organic phases were extracted with 1 M NaOH solution. The aqueous phase was washed with DCM, acidified to pH 1 with 4 N HCl solution and extracted with DCM. The organic phase was washed with saturated NaCl solution, dried over Na2SO4 and evaporated down i.vac. The crude product was used in the next reaction step without any further purification.

後処理

  1. temperatureThe aqueous phase was cooled to RT
  2. extractionexhaustively extracted with EtOAc
  3. extractionThe combined organic phases were extracted with 1 M NaOH solution
  4. washThe aqueous phase was washed with DCM
  5. extractionextracted with DCM
  6. washThe organic phase was washed with saturated NaCl solution
  7. dry with materialdried over Na2SO4
  8. customevaporated down i.vac
  9. customThe crude product was used in the next reaction step without any further purification

出典と根拠

ORDレコード
ord-2a428a71d8774525afa6044660cfdd87
出典データセット
uspto-grants-2009_05
特許番号
US07528129B2

関連ノート

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