Diethyl Ether → 3-tert-Butyl-4-hydroxybenzonitrile

HRID 1505380노트

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HRID 1505380 반응식
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=O)([CH3:4])[CH3:3].Cl.[NH2:15]O.CCOCC>C(O)(=O)C>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[C:8]#[N:15])([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 30176183-(tert-Butyl)-4-hydroxybenzaldehyde2회

생성물 1

HCID 184547233-tert-Butyl-4-hydroxybenzonitrile

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
0 °C

실험 절차

3-(1,1-dimethylethyl)-4-hydroxybenzaldehyde (Intermediate 108, 550 mg) and hydroxylamine hydrochloride (322 mg, 4.63 mmol) were stirred in 8.0 mL of acetic acid at reflux for 1 h. After cooling down to 0° C., the mixture was poured into Et2O and washed once with water and once with NaOH (5% aqueous solution). The collected aqueous phases were extracted with Et2O (two times) and the combined organic phases were dried over Na2SO4, filtered, evaporated and triturated with pentane affording 540 mg of the title compound.

후처리

  1. temperatureat reflux for 1 h
  2. washwashed once with water and once with NaOH (5% aqueous solution)
  3. extractionThe collected aqueous phases were extracted with Et2O (two times)
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customtriturated with pentane affording 540 mg of the title compound

출처 및 근거

ORD 기록
ord-9eed92b7b8eb4fca9d00e881b49f74f4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216967B2

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