Sulfuric Acid → Phenol, 4-(5-octyl-2-pyridinyl)-

HRID 1198834Notes

Reaction equation

HRID 1198834 reaction equation
S(=O)(=O)(O)O.[CH2:6]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:26]=[CH:25][C:23](N)=[CH:22][CH:21]=2)=[N:18][CH:19]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].N([O-])=[O:28].[Na+].[OH-].[Na+]>O>[CH2:6]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:26]=[CH:25][C:23]([OH:28])=[CH:22][CH:21]=2)=[N:18][CH:19]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19867286HCID 19867286, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-Yield 35.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

10 ml of 3N sulphuric acid were treated while stirring with 1.8 g of p-(5-octyl-2-pyridyl)aniline. The mixture was cooled to 5° C. and then treated dropwise at 0°-5° C. within about 3 minutes with a solution of 0.442 g of sodium nitrite in 2 ml of water. The brown mixture obtained was poured into 100 ml of water and heated to reflux for 30 minutes while stirring. The reaction mixture was subsequently cooled to room temperature, adjusted to about pH 5 with 7 ml of 3N sodium hydroxide solution and extracted once with 200 ml of methylene chloride and once with 100 ml of methylene chloride. The organic phases were washed with 150 ml of dilute sodium chloride solution, dried over sodium sulphate and evaporated in a vacuum. The residue (1.867 g) was separated by chromatography on 250 g of silica gel at 0.4 bar with methylene chloride and methylene chloride/acetone. Recrystallization of the resulting red-brown oil in diethyl ether/hexane at 0° C. gave 0.635 g of p-(5-octyl-2-pyridyl)phenol as beige crystals. Working-up of the mother liquor gave 0.355 g of crude p-(5-octyl-2-pyridyl)phenol as a brown oil.

Workup

  1. customThe brown mixture obtained
  2. temperatureheated
  3. temperatureto reflux for 30 minutes
  4. temperatureThe reaction mixture was subsequently cooled to room temperature
  5. extractionextracted once with 200 ml of methylene chloride and once with 100 ml of methylene chloride
  6. washThe organic phases were washed with 150 ml of dilute sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated in a vacuum
  9. customThe residue (1.867 g) was separated by chromatography on 250 g of silica gel at 0.4 bar with methylene chloride and methylene chloride/acetone
  10. customRecrystallization of the resulting red-brown oil in diethyl ether/hexane at 0° C.

Sources & evidence

ORD record
ord-160964ccfb6147fd93e64d94f8c58491
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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