Stearic Acid → 2-Heptadecyl-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Reaction equation

[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:21][C:22]([CH3:26])([CH3:25])[CH2:23]O>>[CH3:23][C:22]1([CH3:26])[CH2:25][O:20][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[N:21]1

Participants

Reactant 2

HCID 5281Stearic Acid

HCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 2268502-Heptadecyl-4,4-dimethyl-4,5-dihydro-1,3-oxazoleYield 79.7%

Procedure

Following example 11, 14.9 g (52.4 mmoles) of octadecanoic acid and 9.34 g (104.8 mmoles) of 2-amino-2-methylpropanol gave 14.1 g (79.7%) of product, b.p. 140°-143° C./0.01 mmHg.

Sources & evidence

ORD record: ord-1cd68335dedf4f7b9317b67a9813b834
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04876249

Reaction notes

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