Triethylamine → HCID 58997533, compound

HRID 1591807Notes

Reaction equation

HRID 1591807 reaction equation
[CH2:1]([C:5]([CH2:10][CH3:11])([CH2:8][OH:9])[CH2:6][OH:7])[CH2:2][CH2:3][CH3:4].[P:12](Cl)(Cl)Cl.[CH2:16]([CH:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([C:5]1([CH2:10][CH3:11])[CH2:6][O:7][P:12]([O:31][CH:28]2[CH2:27][CH2:26][CH:25]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:30][CH2:29]2)[O:9][CH2:8]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24387Phosphorus trichloride2×HCID 610382-Butyl-2-ethyl-1,3-propanediolHCID 783674-Nonylcyclohexan-1-ol

Product 1

HCID 58997533HCID 58997533, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 28 g (0.17 mole) of 2-butyl-2-ethyl-1,3-propandiol in 300 mL of toluene is added dropwise 16 mL (0.17 mole) of phosphorus trichloride at 70° C. After 1 h, the P31-NMR shows that the PCl3 (signal at 220 ppm) is fully reacted and a new product is formed (signal at 150 ppm). The temperature is raised to 80° C. At this temperature a solution of 35.8 g (0.17 mole) 4-nonylcyclohexanol, 200 mL (1.4 mole) of triethylamine in 200 mL of toluene is added rapidly dropwise (approx. 30 min). A suspension is obtained. The P31-NMR—after further 2 h of reaction time—shows that the educt (signal at 150 ppm) is fully reacted and a new product is formed (signal at 123 ppm). After filtration and removal of the toluene (rotary evaporator) the product is isolated. Yield: 68 g (0.165 mol=96% of theory) of the title compound as a crude slight yellow oil; P31-NMR signals at: 124 ppm (major peak); 123 ppm; Total reaction time: 3 h. % P(calc): 7.47; % P (found): 7.24.

Workup

  1. customa new product is formed (signal at 150 ppm)
  2. customA suspension is obtained
  3. customThe P31-NMR—after further 2 h of reaction time—shows that the educt (signal at 150 ppm)
  4. customis fully reacted
  5. customa new product is formed (signal at 123 ppm)
  6. filtrationAfter filtration and removal of the toluene (rotary evaporator) the product
  7. customis isolated

Sources & evidence

ORD record
ord-a8f9a7e32e954419b9fdb3c364c636e7
Source dataset
uspto-grants-2007_11
Patent number
US07291662B2

Reaction notes

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