Sodium Iodide → HCID 54349705, compound

HRID 1198835Notes

Reaction equation

HRID 1198835 reaction equation
[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:22][C@@H:23]([CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[CH3:22][C@@H:23]([CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][N:13]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-HCID 13548107(6S)-1-Bromo-6-methyloctane

Product 1

HCID 54349705HCID 54349705, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-25 °C

Procedure

A mixture of 0.355 g of crude p-(5-octyl-2-pyridyl)-phenol, 10 ml of ethanol, 0.260 g of (S)-6-methyloctyl bromide, 0.172 g of potassium carbonate and a spatula tip of sodium iodide was heated to 90° C. (oil bath temperature) for about 60 hours while stirring. The brown suspension obtained was subsequently cooled and concentrated in a vacuum. The brown oily residue was separated by chromatography on 120 g of silica gel at 0.4 bar with methylene chloride/acetone (vol. 99:1). The resulting brownish paste (0.367 g) was dissolved in about 5 ml of hexane, the solution was filtered and the filtrate was cooled to -25° C. The precipitate was filtered off under suction and distilled at 250° C/0.05 bar, there being obtained 0.122 g of (S)-2-[p-(6-methyloctyloxy)phenyl]-5-octylpyridine as a light yellowish smectic liquid crystal. Concentration of the mother liquor and subsequent distillation gave a further 0.164 g of (S)-2-[p-(6-methyloctyloxy)phenyl]-5-octylpyridine as a light yellowish smectic liquid crystal. The product (total 0.286 g) was treated with diethyl ether, evaporated, dried at 80° C. for 2 hours and again distilled, there being obtained 0.245 g of (S)-2-[p-(6-methyloctyloxy)phenyl]-5-octylpyridine; m.p. (C-S) 36.1° C., phase transition (S--Sc*) 57° C., cl.p. (Sc* --I) 70.4° C.

Workup

  1. customThe brown suspension obtained
  2. temperaturewas subsequently cooled
  3. concentrationconcentrated in a vacuum
  4. customThe brown oily residue was separated by chromatography on 120 g of silica gel at 0.4 bar with methylene chloride/acetone (vol. 99:1)
  5. dissolutionThe resulting brownish paste (0.367 g) was dissolved in about 5 ml of hexane
  6. filtrationthe solution was filtered
  7. filtrationThe precipitate was filtered off under suction
  8. distillationdistilled at 250° C/0.05 bar, there

Sources & evidence

ORD record
ord-cf6910653fc04bee9e1dc7eac15e61b5
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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