Hydrochloric Acid → Phosphorodichloridic acid, octyl ester

HRID 273655Notes

Reaction equation

HRID 273655 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[CH2:6]([OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl>>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 24813Phosphorus oxychloride

Product 1

HCID 6422925Phosphorodichloridic acid, octyl ester

Conditions

Temperature
10 °C

Procedure

Phosphoryl trichloride (3113 g; 20.3 moles) is placed in a 5-liter flask fitted with a condenser and mechanical stirrer, and cooled down to about 10° C. (external ice bath). Octanol (2380 g; 18.3 moles; 0.9 equivalents with respect to POCl3) is added at a rate such that the reaction temperature remains below 15° C. The reaction is exothermic and the HCl gas that evolves during this reaction is vented out with a flow of nitrogen through an aspirator operated with a slight vacuum of about 0.5 inches of mercury. When addition of alcohol is completed (2-3 hours), the ice bath is removed and the reaction mixture is allowed to warm to room temperature and then warmed to 60°-70° C. and stirred at this temperature for 1.5 hours to drive out most of the HCl gas. The product, octyl phosphorodichloridate, is obtained as a clear light yellow free-flowing liquid.

Workup

  1. customfitted with a condenser and mechanical stirrer
  2. customremains below 15° C
  3. custom(2-3 hours)
  4. customthe ice bath is removed
  5. temperatureto warm to room temperature
  6. temperaturewarmed to 60°-70° C.

Sources & evidence

ORD record
ord-400f8f4888844ec784291124f68afe7d
Source dataset
uspto-grants-1995_02
Patent number
US05387352

Reaction notes

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