Urea → 3-Amyl-3-hydroxymethyloxetane

HRID 1058150Notes

Reaction equation

HRID 1058150 reaction equation
[CH2:1]([C:3]([CH2:11][OH:12])([CH2:9][OH:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])O.C(N)(N)=O.[OH-].[K+]>>[OH:10][CH2:9][C:3]1([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:1][O:12][CH2:11]1

Participants

4

Reactant 3

HCID 1176UreaHCID 14797Potassium HydroxideHCID 13760613Trimethylolhexane

Product 1

HCID 186732153-Amyl-3-hydroxymethyloxetaneYield 24.4%

Conditions

Temperature
215 °C

Procedure

84.5 mmoles of trimethylolhexane and 70.9 mmoles of carbamide were together with 1.2 mole % of potassium hydroxide (based on total amount of reactants and catalysts) charged in a reaction vessel. The synthesis was performed in accordance with Example 1. The temperature uring the pyrolysis gradually raised to 215° C. 20.6 mmoles of 3-hydroxymethyl-3-pentyloxetane (trimethylolhexane oxetane) was yielded from the distillate and characterised by NMR. The remainder contained the spiro-orthocarbonate (3% on the carbamide) yielded as by-product.

Workup

  1. additioncharged in a reaction vessel

Sources & evidence

ORD record
ord-01f51a6f0f1b4129801b9e83bb1b7562
Source dataset
uspto-grants-2003_02
Patent number
US06515152B1

Reaction notes

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