Methanol → HCID 23470674, compound

HRID 127981Notes

Reaction equation

HRID 127981 reaction equation
[CH3:1][OH:2].C(N(CC)CC)C.[P:10](Cl)([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:11].Cl.C(N(CC)CC)C.ClCl>C1(C)C=CC=CC=1>[P:10]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([O:2][CH3:1])=[O:11]

Participants

7

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 24526ChlorineHCID 18366352HCID 18366352, compound

Product 1

HCID 23470674HCID 23470674, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5 g. (0.15 mole) of methanol and 12.12 g. (0.12 mole) of triethylamine in 200 ml. of toluene was stirred at ambient temperature (22° C.) and a total of 45.25 g. (0.1 mole) of dilauryl chlorophosphate (prepared as described in Preparation 1) was added dropwise over a period of 13 minutes. After the addition was complete, the reaction mixture was stirred for a further 1.5 hour at ambient temperature before being filtered to remove triethylamine hydrochloride (7.85 g.). The filtrate was heated to 95° C. for a few minutes before being cooled to 5° C. and filtered. The solid so isolated was a further 2.82 g. of triethylamine hydrochloride. The filtrate was evaporated to dryness and the residue was triturated with 150 ml. of ether. The insoluble material (triethylamine hydrochloride; 0.33 g.; total triethylamine hydrochloride=11 g.=80 percent theoretical) was removed by filtration and the filtrate was evaporated to dryness to yield 44 g. of methyl dilaurylphosphate which was found to contain 0.09 percent of hydrolyzable chlorine corresponding to the presence of 1.15 percent of starting material (dilauryl chlorophosphate).

Workup

  1. additionAfter the addition
  2. filtrationbefore being filtered
  3. customto remove triethylamine hydrochloride (7.85 g.)
  4. temperatureThe filtrate was heated to 95° C. for a few minutes
  5. temperaturebefore being cooled to 5° C.
  6. filtrationfiltered
  7. customThe solid so isolated
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was triturated with 150 ml
  10. customThe insoluble material (triethylamine hydrochloride; 0.33 g.; total triethylamine hydrochloride=11 g.=80 percent theoretical) was removed by filtration
  11. customthe filtrate was evaporated to dryness
  12. customto yield 44 g

Sources & evidence

ORD record
ord-9e79b80ee42f45398e63641752990756
Source dataset
uspto-grants-1981_03
Patent number
US04257996

Reaction notes

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