Stearoyl chloride → HCID 20249612, compound

HRID 1077116Notes

Reaction equation

HRID 1077116 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][O:9][P:6]([O:7][CH2:8]1)[O:5][CH2:4]2.[C:11](Cl)(=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(N(CC)CC)C>C1(C)C=CC=CC=1>[P:6]12[O:9][CH2:10][C:3]([CH2:2][O:1][C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH2:8][O:7]1)[CH2:4][O:5]2

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 2001832,6,7-Trioxa-1-phosphabicyclo(2.2.2)octane-4-methanol

Product 1

HCID 20249612HCID 20249612, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

16.4 g (0.1 mol) of 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane are dissolved in 150 ml of toluene by warming. 30.2 g (0.1 mol) of stearic acid chloride, followed by 10.1 g (0.1 mol) of triethylamine, are added dropwise at room temperature. After the slight evolution of heat has died away, the mixture is stirred for 10 hours under nitrogen at room temperature and the precipitated triethylamine hydrochloride is then filtered off. The filtrate is evaporated with exclusion of moisture, a yellowish oil remaining, which crystallises on being triturated with methanol. After filtering off under suction and drying, stearic acid 1-phospha-2,6,7-trioxabicyclo[2,2,2]oct-4-yl-methyl ester (Stabiliser No. 9), melting point 49°C, is obtained.

Workup

  1. temperatureby warming
  2. additionare added dropwise at room temperature
  3. temperatureAfter the slight evolution of heat
  4. filtrationthe precipitated triethylamine hydrochloride is then filtered off
  5. customThe filtrate is evaporated with exclusion of moisture
  6. customwhich crystallises
  7. customon being triturated with methanol
  8. filtrationAfter filtering off under suction
  9. customdrying

Sources & evidence

ORD record
ord-c2a9fb2568c74e0e9c13a88c9bb1392a
Source dataset
uspto-grants-1976_05
Patent number
US03959413

Reaction notes

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