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Water → 2,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

HRID 615034
Notes
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Reaction equation

HRID 615034 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].[OH-].[Na+].I[CH2:30][CH:31]([OH:34])[CH2:32][OH:33].O>CN(C)P(N(C)C)(N(C)C)=O.CCOCC>[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 472634-(Hexadecylamino)benzoic acidHCID 921273-Iodo-1,2-propanediol

Product 1

HCID 130193802,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 7.34 g of 4-(n-hexadecylamino)benzoic acid, 4.80 g of 25% aqueous sodium hydroxide, and 12.6 g of 3-iodo-1,2-propanediol in 50 ml of hexamethylphosphoramide is stirred for 24 hours at ambient temperature, diluted with 100 ml of ether and stirred for 5 days at ambient temperature. The mixture is treated with water and extracted with ether. The dried extracts are evaporated to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate, m.p. 112° C.

Workup

  1. extractionextracted with ether
  2. customThe dried extracts are evaporated

Sources & evidence

ORD record
ord-399e40577ffd49b787a22b9d1d03161c
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04146546

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes