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

HRID 1023578
Notes
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Reaction equation

HRID 1023578 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 30176183-(tert-Butyl)-4-hydroxybenzaldehyde2×

Product 1

HCID 184547233-(tert-Butyl)-4-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bd3f778c84014a1b960f2dbeb439333b
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722695B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes