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

HRID 1439283Notes

Reaction equation

HRID 1439283 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:27][CH2:28][CH:29]([CH2:31]O)[OH:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:31][CH:29]([OH:30])[CH2:28][OH:27])=[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

6

Reactant 4

HCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 472634-(Hexadecylamino)benzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 722 mg of 4-(n-hexadecylamino)benzoic acid, 736 mg of glycerol, and 412 mg of p-toluene sulfonic acid is heated for 4 hours at 120° C, allowed to cool, and then is treated with ether and 2% aqueous sodium carbonate solution. Filtration affords a white solid which is recrystallized from chloroform to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate, mp 112° C.

Workup

  1. temperatureto cool
  2. filtrationFiltration
  3. customaffords a white solid which
  4. customis recrystallized from chloroform

Sources & evidence

ORD record
ord-6ac1ecacad67487f9a4989af1d2e6376
Source dataset
uspto-grants-1977_11
Patent number
US04058550

Reaction notes

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