Stearyl Alcohol → 2,2-Bis(hydroxymethyl)-3-octadecylhenicosane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite

HRID 1578057Notes

Reaction equation

HRID 1578057 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N([CH2:25][CH3:26])CC)C.[OH:27][P:28]([O:30][P:31]([OH:33])[OH:32])[OH:29].Cl[C:35](Cl)([C:37]([CH2:42][OH:43])([CH2:40][OH:41])[CH2:38][OH:39])[OH:36]>C1(C)C=CC=CC=1>[OH:27][P:28]([O:30][P:31]([OH:33])[OH:32])[OH:29].[CH2:1]([C:35]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:25][CH3:26])([C:37]([CH2:42][OH:43])([CH2:40][OH:41])[CH2:38][OH:39])[OH:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8221Stearyl AlcoholHCID 8471TriethylamineHCID 131712417Dichloropentaerythritol diphosphite

Product 1

HCID 1317124162,2-Bis(hydroxymethyl)-3-octadecylhenicosane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 567 g. (2.1 mols) of octadecyl alcohol and 212 g. (2.1 mols) of triethyl amine in 1800 ml. of toluene, at 30° C., there is added a solution of 265 g. (1.0 mol) of dichloropentaerythritol diphosphite in 600 ml. of toluene; the addition is made portionwise over a period of one hour, then the mixture is warmed with continued stirring at 45°-50° C. The cooled mixture is filtered to separate the triethylamine hydrochloride and the filtrate is stripped of toluene to a final temperature of 85° C./20 mm. The solid residue consitutes a quantitative yield of distearyl pentaerythritol diphosphite, M.P., 68°-70° C.

Workup

  1. additionthe addition
  2. temperaturethe mixture is warmed
  3. filtrationThe cooled mixture is filtered
  4. customto separate the triethylamine hydrochloride
  5. customtemperature of 85° C./20 mm

Sources & evidence

ORD record
ord-fd36029c4b1745b5aac4a3cde5f27c47
Source dataset
uspto-grants-1981_09
Patent number
US04290976

Reaction notes

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