Ammonia → 2-[4-Isopropenyl-3-Pyridyl]-5-(3-Methyl-2-Octyl) Resorcinol

HRID 328692Notes

Reaction equation

HRID 328692 reaction equation
C([C:4]1([CH:11]=[C:10]([CH:12]([CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13])[CH2:9][C:7](C(=O)C)([OH:8])[CH:6]1[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:29]=1[C:30]([CH3:32])=[CH2:31])[OH:5])(=O)C.N>C1(C)C=CC=CC=1>[C:30]([C:29]1[CH:28]=[CH:27][N:26]=[CH:25][C:24]=1[C:6]1[C:4]([OH:5])=[CH:11][C:10]([CH:12]([CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13])=[CH:9][C:7]=1[OH:8])([CH3:32])=[CH2:31]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 706382701,3-Diacetyl-2-[4-Isopropenyl-3-Pyridyl]-5-(3-Methyl-2-Octyl)Resorcinol

Product 1

HCID 542791802-[4-Isopropenyl-3-Pyridyl]-5-(3-Methyl-2-Octyl) Resorcinol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.37 g. of 1,3-diacetyl-2-[4-isopropenyl-3-pyridyl]-5-(3-methyl-2-octyl)resorcinol in 50 ml. of toluene was placed in a high pressure bomb with 40 ml. of liquid ammonia. The mixture was shaken at room temperature overnight. The excess ammonia was allowed to escape; the residue was triturated with water and extracted with chloroform. The chloroform extracts were washed twice with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was recrystallized from ether-petroleum ether (30°-60°) to yield the pure product; m.p. 128°-129°.

Workup

  1. customthe residue was triturated with water
  2. extractionextracted with chloroform
  3. washThe chloroform extracts were washed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ether-petroleum ether (30°-60°)
  7. customto yield the pure product

Sources & evidence

ORD record
ord-ed1edd042c924694b5da947687235825
Source dataset
uspto-grants-1977_04
Patent number
US04018777

Reaction notes

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