Hydrochloric Acid → 2-Ethyl-6-methylphenol

HRID 643116

반응식

HRID 643116 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 5193332-Ethyl-6-methylphenol

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-568046a471604e33b46dcfc8c8266ce2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696209B2

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