Triethylamine → (+/-)-Phenyl Nonyl Phosphoryl Chloride

HRID 247830

Reaction equation

HRID 247830 reaction equation
[C:1]1([P:7]([Cl:10])(Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1>[C:1]1([P:7]([Cl:10])([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89141-NonanolHCID 69990Phenylphosphonic dichloride

Product 1

HCID 86746784(+/-)-Phenyl Nonyl Phosphoryl ChlorideYield 110.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of phenylphosphonic dichloride (3.0 g, 14.2 mmol) and triethylamine (2.4 mL, 17.1 mmol) in toluene (20 mL) at 0° C. is added dropwise a solution of 1-nonanol (2.05 g, 14.2 mmol) in toluene (5 mL). The mixture is allowed to warm slowly to room temperature and stirred for 2 hours. The mixture is filtered, and the filtrate is concentrated to afford 4.5 g of the title compound as a light yellow liquid; 1H NMR (200 MHz, CDCl3)δ7.40-7.15 (m, 5 H), 4.40-4.25 (m, 2 H), 1.90-1.65 (m, 2 H), 1.45-1.20 (m, 12 H), 0.89 (t, J=7 Hz, 3 H).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-eb05f0261fa34498bd47e9ca295cb156
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Linked notes

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