Water → 4,5-Dihydro-4-methyl-2-undecyl-4-oxazolemethanol

HRID 1086426Notes

Reaction equation

HRID 1086426 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][C:16]([CH3:21])([CH2:19]O)[CH2:17][OH:18].O>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[OH:18][CH2:17][C:16]1([CH3:21])[CH2:19][O:14][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[N:15]1

Participants

6

Reactant 3

HCID 962WaterHCID 15312-Amino-2-methyl-1,3-propanediolHCID 3893Lauric Acid

Product 1

HCID 735074,5-Dihydro-4-methyl-2-undecyl-4-oxazolemethanolYield 84.6%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20.03 g (100 mmoles) of dodecanoic acid and 11.57 g (110) mmoles) of 2-amino-2-methyl-1,3-propanediol in 10 ml of xylene was heated for 30 hours at 185°-190° C. with azeotropic removal of water. The reaction mixture was taken up in ethyl acetate and was washed with water to remove excess amino alcohol. The organic layer was dried, concentrated and the residue was distilled at 152°-155° C./1 mm Hg to give 22.8 g (84.6%) of 4-hydroxymethyl-4-methyl-2-undecyl-2-oxazoline.

Workup

  1. washwas washed with water
  2. customto remove excess amino alcohol
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. distillationthe residue was distilled at 152°-155° C./1 mm Hg

Sources & evidence

ORD record
ord-9176830619b64ac88ef7d939db3bed6d
Source dataset
uspto-grants-1991_07
Patent number
US05030629

Reaction notes

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