Palmitic Acid → Tert-butyl 3-hexadecanoyloxyoctadecanoate

HRID 1903520Notes

Reaction equation

[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:26](O)(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[C:26]([O:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

Reactant 2

HCID 985Palmitic Acid

HCID 13962663Tert-butyl 3-hydroxyoctadecanoate

Product 1

HCID 20216792Tert-butyl 3-hexadecanoyloxyoctadecanoateYield 96.5%

Procedure

tert-Butyl 3-hydroxyoctadecanoate (1.068 g) was acylated by the acid chloride derived from hexadecanoic acid (3.84 g) according to similar manner to that of Preparation 1-(2) to give an oil of tert-butyl 3-hexadecanoyloxyoctadecanoate (1.72 g).

Workup

customof Preparation 1-(2)

Sources & evidence

ORD record: ord-e7274fd01095464cb9a5695a65269cc8
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04436726

Reaction notes

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