Phosphorus pentachloride → 4-n-Octyloxyphenylacetyl chloride

HRID 248300Notes

Reaction equation

HRID 248300 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[CH2:7]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([Cl:2])=[O:25])=[CH:18][CH:17]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 123873512-[4-(Octyloxy)phenyl]acetic acid

Product 1

HCID 151314654-n-Octyloxyphenylacetyl chloride

Conditions

Temperature
80 °C

Procedure

Phosphorus pentachloride (1.lg, 0.0053 mol) was added to 4-n-octyloxyphenylacetic acid (1.3g, 0.0049 mol) and the mixture was allowed to react by heating at 80° C. POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo to obtain 4-n-octyloxyphenylacetyl chloride. This chloride was dissolved in toluene (10 ml) and to the mixture were added S-(-)-α-(4-n-heptyloxyphenyl)ethyl alcohol (1.0g, 0.0042 mol) and pyridine (1 ml, a dehydrochlorinating agent). The mixture was permitted to stand for 10 hours at room temperature, warmed at 60° C. and maintained as such for 3 hours, and then cooled. The resulting mixture was added to diluted hydrochloric acid and the resultant was extracted with ether. The ether layer was washed with an aqueous solution of NaHCO3 and then with water, and dried over Na2SO4. The ether was distilled off and the residue was purified by means of a column chromatography (solvent : chloroform) and the resultant was recrystallized from ethanol to obtain the above compound of α-(4-n-heptyloxyphenyl)ethyl 4-n-octyloxyphenylacetate. The infrared spectrum of this compound is shown in FIG. 3. This compound did not show any liquid crystalline phase, and it was a liquid at room temperature. The angle of rotation [α]25D of the compound was -52.4° (solvent : chloroform).

Workup

  1. customto react
  2. customPOCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo

Sources & evidence

ORD record
ord-17f036b31b814c5db6d733b67d8ec597
Source dataset
uspto-grants-1993_05
Patent number
US05209867

Reaction notes

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