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

HRID 527726ノート

反応式

HRID 527726 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 184547233-tert-Butyl-4-hydroxybenzonitrile

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

3-(1,1-dimethylethyl)-4-hydroxybenzaldehyde (Reference Intermediate R9, 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.

後処理

  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

出典と根拠

ORDレコード
ord-e425a0b31491473a978a11c1a7559c88
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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