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

HRID 2352199Notes

Reaction equation

HRID 2352199 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-1,3propanediol 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 mmHg to give 22.8 g (84.6%) of 4-hydroxymethyl-4-methyl-2-undecyl-2oxazoline.

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 mmHg

Sources & evidence

ORD record
ord-60fe064ac7264cf1aefd49c9da80aac9
Source dataset
uspto-grants-1989_10
Patent number
US04876249

Reaction notes

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