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Water → 3-Hydroxyacetonyl 4-(n-hexadecylamino)benzoate

HRID 1439304
Notes
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Reaction equation

HRID 1439304 reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[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][CH3:17].O[CH:29]([OH:33])[C:30](=[O:32])[CH3:31].C(Cl)(Cl)Cl.[OH2:38]>CN(C)C1C=CN=CC=1>[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:38][CH2:31][C:30]([CH2:29][OH:33])=[O:32])=[O:24])=[CH:21][CH:20]=1)[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][CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 131809821,1-Dihydroxypropan-2-oneHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 213269523-Hydroxyacetonyl 4-(n-hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 14284
4-(Dimethylamino)pyridine
Catalyst

Procedure

The compound 4-(n-hexadecylamino)benzoyl chloride hydrochloride (4.16 g.) is added to a mixture of 3.6 g. of dihydroxyacetone and 2.44 g. of 4-dimethylaminopyridine in an ice bath. After 4 hours at room temperature, the mixture is treated with chloroform and water. The chloroform extract is chromatographed rapidly and evaporated in vacuo to yield 3-hydroxyacetonyl 4-(n-hexadecylamino)benzoate.

Workup

  1. extractionThe chloroform extract
  2. customis chromatographed rapidly
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-78bdaf4a1d0f41f4aa4fa4349056d8f7
Source dataset
uspto-grants-1977_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04058550

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes