Sodium Hydroxide → HCID 14069925, compound

HRID 3932Notes

Reaction equation

HRID 3932 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:11]=2)=[CH:6][CH:5]=1.Br[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O>[CH3:35][C@H:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:26][CH2:25][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-HCID 14069923(R)-1-bromo-(4-methyl)decane

Product 1

HCID 14069925HCID 14069925, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of a 30% aqueous solution of sodium hydroxide was added dropwise to a mixture of 2 g (0.007 mol) of 2-(p-hydroxyphenyl)-5-octylpyridine and 1.65 g (0.007 mol) of (R)-1-bromo-(4-methyl)decane with stirring. The resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours. 150 ml of water was added to the reaction solution and the organic layer was extracted with chloroform. After washing the extract three times with water, chloroform was removed by distillation. The residue was chromatographed over 2.5×100 (cm) of silica gel and developed with hexane and benzene. The effluent was repeatedly recrystallized from a mixture of methanol and acetone to yield 1.44 g (0.0033 mol) of (R)2-[p-(4-methyldecyloxy)phenyl]-5-octylpyridine.

Workup

  1. temperatureThe resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours
  2. extractionthe organic layer was extracted with chloroform
  3. washAfter washing the
  4. extractionextract three times with water, chloroform
  5. customwas removed by distillation
  6. customThe residue was chromatographed over 2.5×100 (cm) of silica gel
  7. customThe effluent was repeatedly recrystallized from a mixture of methanol and acetone

Sources & evidence

ORD record
ord-db779db8732644f49d9a577c43124856
Source dataset
uspto-grants-1988_02
Patent number
US04723018

Reaction notes

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