Pyridine → N-[(5-tert-Butyl-2-hydroxyphenyl)methyl]acetamide

HRID 364896Notes

Reaction equation

HRID 364896 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14].N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>O1CCOCC1>[C:21]([NH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:11])([CH3:13])[CH3:12])[CH:7]=[CH:6][C:5]=1[OH:14])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 212969502-(Aminomethyl)-4-tert-butylphenol hydrochloride

Product 1

HCID 13210348N-[(5-tert-Butyl-2-hydroxyphenyl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

43 g (0.2 mole) of 2-aminomethyl-4-(1,1-dimethylethyl)-phenol hydrochloride are suspended in 400 ml of 1,4-dioxane, and 40 ml of pyridine are added. 40 ml (0.55 mole) of acetyl chloride are added dropwise while stirring and cooling with ice. The mixture is then stirred for 2.5 hours at 90° and poured into ice water, and the precipitate which has crystallized out is filtered off with suction.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture is then stirred for 2.5 hours at 90°
  3. customthe precipitate which has crystallized out
  4. filtrationis filtered off with suction

Sources & evidence

ORD record
ord-dcd443eda4674388a7bbb90b3deda725
Source dataset
uspto-grants-1986_08
Patent number
US04607030

Reaction notes

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