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

HRID 1439297Notes

Reaction equation

HRID 1439297 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 recrystallization from acetonitrile.

Workup

  1. customthe ether layer is separated
  2. extractionthe ether extraction
  3. customevaporation of the ether
  4. additionthe mixture of starting material
  5. custom2,3-dihydroxypropyl ester is separated by chromatography on silica gel and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-f189ecdda7d648c7958e34d55723315d
Source dataset
uspto-grants-1977_11
Patent number
US04058550

Reaction notes

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