Epichlorohydrin → 2,3-Epoxypropyl 4-(n-hexadecylamino)benzoate

HRID 615044Notes

Reaction equation

[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH2:6]([NH:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([O-:29])=[O:28])=[CH:25][CH:24]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[Na+].CN(C)P(N(C)C)(N(C)C)=O>O>[CH2:6]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:1][CH:3]2[O:5][CH2:4]2)=[O:28])=[CH:30][CH:31]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 89.0 g of epichlorohydrin, 92.0 g of sodium 4-(n-hexadecylamino)benzoate, and 350 ml of hexamethylphosphoramide is stirred at 105° C. for 5 hours, allowed to cool, and poured into 1.0 liter of water. The white solid is collected by filtration, recrystallized from acetonitrile and then from hexane-methylene chloride to yield 2,3-epoxypropyl 4-(n-hexadecylamino)benzoate, mp 86°-89° C.

Workup

temperatureto cool
filtrationThe white solid is collected by filtration
customrecrystallized from acetonitrile

Sources & evidence

ORD record: ord-155ac92aee65436a99ae530899e56e17
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146546

Reaction notes

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