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

HRID 615055Notes

Reaction equation

HRID 615055 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].[O:27]1[CH2:31][CH:28]1[CH2:29][OH:30].CN(C)P(N(C)C)(N(C)C)=O.CCOCC>O>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:31][CH:28]([OH:27])[CH2:29][OH:30])=[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 3283Diethyl EtherHCID 11164GlycidolHCID 12679HexamethylphosphoramideHCID 472634-(Hexadecylamino)benzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.6 g. of 4-(n-hexadecylamino)benzoic acid and 1.0 g. of 2,3-epoxypropan-1-ol in 100 ml. of hexamethylphosphoramide is heated at 90° C. for 8 hours. After addition of ether and water, the ether layer is separated and the ether extraction repeated several times. Following evaporation of the ether extracts, the mixture of starting material and desired 2,3-dihydroxypropyl ester is separated by chromatography on silica gel and recrystallized from acetonitrile.

Workup

  1. customthe ether layer is separated
  2. extractionthe ether extraction
  3. customevaporation of the ether
  4. additionthe mixture of starting material and desired 2,3-dihydroxypropyl ester
  5. customis separated by chromatography on silica gel
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-8f27c904425c4ddbab943734b5489298
Source dataset
uspto-grants-1979_03
Patent number
US04146546

Reaction notes

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