3-Chloro-1,2-propanediol → 2,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

HRID 1439278Notes

Reaction equation

[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=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][CH3:16].[H-].[Na+].Cl[CH2:30][CH:31]([OH:34])[CH2:32][OH:33]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:30][CH:31]([OH:34])[CH2:32][OH:33])=[O:23])=[CH:25][CH:26]=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][CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 7.20 g of 4-(n-hexadecylamino)benzoic acid in 25 ml of hexamethylphosphoramide is added to a stirred mixture of 0.800 g of sodium hydride (57% in mineral oil) and 25 ml of hexamethylphosphoramide. The soluion which forms after one hour is treated with 11.0 g of 1-chloro-2,3-propanediol and is then stirred at 60° C for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate melting at 112°-113° C.

Workup

filtrationDilution with water followed by filtration
customaffords a white solid which
customis crystallized from ethanol

Sources & evidence

ORD record: ord-bc4554a7691b41e1968dd906060a310b
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04058550

Reaction notes

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