Trimethylolpropane diallyl ether → [3-(2-Hydroxymethyl-2-{3-[hydroxy-(2,4,4-trimethylpentyl)-phosphinoyl]-propoxymethyl}-butoxy)-propyl]-(2,4,4-trimethylpentyl)-phosphinic acid

HRID 1661854

Reaction equation

HRID 1661854 reaction equation
[CH3:1][CH:2]([CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:3][PH:4](=[O:6])[OH:5].[CH3:12][CH2:13][C:14]([CH2:22][O:23][CH2:24][CH:25]=[CH2:26])([CH2:17][O:18][CH2:19][CH:20]=[CH2:21])[CH2:15][OH:16]>C(OOC(CC)(C)C)(CC)(C)C>[OH:16][CH2:15][C:14]([CH2:17][O:18][CH2:19][CH2:20][CH2:21][P:4]([OH:6])([CH2:3][CH:2]([CH3:1])[CH2:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:5])([CH2:13][CH3:12])[CH2:22][O:23][CH2:24][CH2:25][CH2:26][P:4]([CH2:3][CH:2]([CH3:1])[CH2:7][C:8]([CH3:10])([CH3:9])[CH3:11])(=[O:5])[OH:6]

Participants

4

Reactant 2

HCID 61196Trimethylolpropane diallyl etherHCID 178460681HCID 178460681, compound

Product 1

HCID 57909086[3-(2-Hydroxymethyl-2-{3-[hydroxy-(2,4,4-trimethylpentyl)-phosphinoyl]-propoxymethyl}-butoxy)-propyl]-(2,4,4-trimethylpentyl)-phosphinic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 25320Di-tert-amyl peroxideCatalyst

Conditions

Temperature
140 °C

Procedure

10 g (0.056 moles) of 2,4,4-trimethylpentyl phosphinic acid, 6.01 g (0.028 moles) of trimethylolpropane diallyl ether and 0.4 mL (0.0019 moles) of di-tert-amylperoxide are mixed in a 100 mL single neck flask. The mixture is purged with argon to remove oxygen and is heated under argon for 6 hours at 140° C. Tert-amyl alcohol is removed by distillation and 16 g (quantitative yield) of [3-(2-hydroxymethyl-2-{3-[hydroxy-(2,4,4-trimethylpentyl)-phosphinoyl]-propoxymethyl}-butoxy)-propyl]-(2,4,4-trimethylpentyl)-phosphinic acid is obtained as a viscous oil.

Workup

  1. customThe mixture is purged with argon
  2. customto remove oxygen
  3. customTert-amyl alcohol is removed by distillation

Sources & evidence

ORD record
ord-32b83ec0f54242348999164dcb2f3216
Source dataset
uspto-grants-2011_10
Patent number
US08030435B2

Linked notes

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