Hydrogen Peroxide → HCID 21412684, compound

HRID 2071832Notes

Reaction equation

HRID 2071832 reaction equation
[O:1]1[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:2]1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[OH:20]O>[Pt].CO>[OH:1][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][N+:14]1([O-:20])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 8083MorpholineHCID 13734243HCID 13734243, compound

Product 1

HCID 21412684HCID 21412684, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

20 grams of 1,2-epoxydodecene (b.p. 97°-98° C. at 3.5 mm Hg A) is heated with 9.7 grams of morpholine at 100° C. in a sealed container for 16 hours. The resulting mixture is then fractionally distilled and the product is collected at a temperature of 119° C. and a pressure of 0.05 mm Hg A. 23.4 grams of N-2-hydroxydodecyl-morpholine having an equivalent weight of 273, by titration (as compared to the calculated equivalent weight of 271 for this compound) are obtained. This product (23.4 grams) is mixed with 9.74 grams of aqueous 30% hydrogen peroxide and 50 ml of methanol and heated at 50° C. for 2 hours. Thereafter any excess peroxide is decomposed by adding 0.1 gram platinum black on charcoal (of 5% Pt content) and heating the mixture at 40° C. for 4 hours. The platinum-on-charcoal catalyst is filtered off, and the filtrate is evaporated to recover the crude product, which is then recrystallized from 300 ml of acetone to produce 17.5 grams of purified N-2-hydroxydodecyl-morpholine N-oxide having a melting point of 151°-2° C. (and having an equivalent weight by potentiometric titration in methanol, equivalence point at pH 3.25, of 290; as compared to the calculated equivalent weight of 287 for this compound).

Workup

  1. distillationThe resulting mixture is then fractionally distilled
  2. customthe product is collected at a temperature of 119° C.
  3. customare obtained
  4. temperatureheating the mixture at 40° C. for 4 hours
  5. filtrationThe platinum-on-charcoal catalyst is filtered off
  6. customthe filtrate is evaporated
  7. customto recover the crude product, which
  8. customis then recrystallized from 300 ml of acetone

Sources & evidence

ORD record
ord-96f38c73034048c7833f7574ade11d18
Source dataset
uspto-grants-1977_09
Patent number
US04048338

Reaction notes

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