Ethanolamine → HCID 11771289, compound

HRID 2309311Notes

Reaction equation

HRID 2309311 reaction equation
[C:1](#[N:19])[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].[CH2:20]([CH2:22]N)[OH:21]>C(Cl)Cl.O.O.C([O-])(=O)C.[Cd+2].C([O-])(=O)C>[CH2:2]([C:1]1[O:21][CH2:20][CH2:22][N:19]=1)[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 2

HCID 700EthanolamineHCID 12532Octadecanenitrile

Product 1

HCID 11771289HCID 11771289, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 6537495Cadmium acetate, dihydrateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

A stirred mixture of about 50.0 grams (0.19 mole) stearonitrile, about 11.7 grams (0.19 mole) ethanolamine, and about 1.2 grams (0.0048 mole) cadmium acetate dihydrate is heated at about 115 degrees C. to about 125 degrees C. under nitrogen for about 88 hours. The mixture is cooled and then dissolved in about 450 ml of methylene chloride and dried over magnesium sulfate. The mixture is then filtered. Residual solvent is removed from the filtrate by vacuum. About 58.6 grams of light yellow solid is obtained. The solid is recrystallized from about 300 ml of hexane. The recrystallized material is collected, washed, and dried, yielding about 4.7 grams with a melting point of about 77 degrees C. to about 90 degrees C. The resulting filtrate, rinses, material removed in the initial filtration step and about 200 ml additional hexane are combined, heated, and filtered using gravity. The product is stored in a refrigerator for several days. The formed crystals are collected, rinsed, and dried at 50 degrees C. under vacuum, yielding about 36.3 grams of white solid with a melting point of about 50 degrees C. to about 54 degrees C.

Workup

  1. customto about 125 degrees C
  2. temperatureThe mixture is cooled
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe mixture is then filtered
  5. customResidual solvent is removed from the filtrate by vacuum

Sources & evidence

ORD record
ord-f25ccc8d60cf4322a4a88e39378f99f0
Source dataset
uspto-grants-1987_09
Patent number
US04695295

Reaction notes

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