Sulfuric Acid → HCID 178443321, compound

HRID 1030026Notes

Reaction equation

HRID 1030026 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:24]([CH:34]([CH2:37]O)[CH2:35][OH:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:24]([C@@H:34]1[CH2:35][O:36][C@@H:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=3)=[N:21][CH:20]=2)[O:23][CH2:37]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 115140411,3-Propanediol, 2-decyl-HCID 19821238HCID 19821238, compound

Product 1

HCID 178443321HCID 178443321, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.2 g of 6-[4-(octyloxy)phenyl]-3-pyridinecarboxaldehyde (prepared in accordance with Example 2) and 1.4 g of 2-decyl-1,3-propanediol in 40 ml of toluene was treated with 5 drops of 10 percent (v/v) sulfuric acid. The mixture was heated to boiling for 1 hour, moist toluene being distilled off and being replaced by fresh toluene. The reaction mixture was then neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on 60 g of silica gel with hexane/ethyl acetate (vol. 9:1) and repeated recrystallization of the trans/cis mixture from ethyl acetate gave 0.56 g of pure 5-(trans-5-decyl-1,3-dioxan-2-yl)-2-[4-(octyloxy)phenyl]pyridine; m.p. (C-S) 69.7° C., transition S-SC 137.5° C., cl.p. (SC -I) 179° C.

Workup

  1. temperatureThe mixture was heated
  2. distillationmoist toluene being distilled off
  3. temperatureafter cooling
  4. washwashed three times with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on 60 g of silica gel with hexane/ethyl acetate (vol. 9:1)
  8. customrecrystallization of the trans/cis mixture from ethyl acetate

Sources & evidence

ORD record
ord-20e92b1986304f4fa1fd49847c80af6a
Source dataset
uspto-grants-1992_04
Patent number
US05104569

Reaction notes

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