Formaldehyde → 3-(beta-Hydroxypropyl)tetrahydro-1,3-oxazine

HRID 2398035Notes

Reaction equation

HRID 2398035 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6]CCO.C=[O:11].[C:12]1([CH3:18])[CH:17]=CC=CC=1>>[OH:11][CH:12]([CH3:18])[CH2:17][N:5]1[CH2:4][CH2:3][CH2:2][O:1][CH2:6]1

Participants

4

Reactant 3

HCID 712Formaldehyde2×HCID 1140TolueneHCID 106986Dipropanolamine

Product 1

HCID 214343563-(beta-Hydroxypropyl)tetrahydro-1,3-oxazine

Conditions

Temperature
90 °C

Procedure

To a glass reaction vessel equipped with stirrer, thermometer, and condenser fitted with a water trap is added di-(3-hydroxypropyl) amine (3.0 mole, 399 g.) and toluene (500 g.). Paraformaldehyde (3.15 mole, 90% pure, 105 g.) is weighed out and about 1/3 is added to the amine solution. The resulting mixture is stirred and heated to 90° C. while slowly adding the remaining paraformaldehyde in about 70 minutes. The reaction is heated to reflux and the water separated. After 4 hours, a total of 63 ml. of water is removed. Toluene is removed at reduced pressure. The residue is distilled at high vacuum to yield 3-(β-hydroxypropyl)tetrahydro-1,3-oxazine.

Workup

  1. customTo a glass reaction vessel
  2. customequipped with stirrer
  3. customthermometer, and condenser fitted with a water trap
  4. temperatureThe reaction is heated
  5. temperatureto reflux
  6. customthe water separated
  7. customof water is removed
  8. customToluene is removed at reduced pressure
  9. distillationThe residue is distilled at high vacuum

Sources & evidence

ORD record
ord-610d73d0d4ef4c908c5295fff4193b88
Source dataset
uspto-grants-1977_05
Patent number
US04024117

Reaction notes

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