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

HRID 615054Notes

Reaction equation

HRID 615054 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O-: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].[Na+].[CH2:28]([CH:30]1[O:32][CH2:31]1)Cl.O.S(=O)(=O)(O)[OH:35]>CN(C)P(N(C)C)(N(C)C)=O.C1C=CC=CC=1.C(COC)OC>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:28][CH:30]([OH:32])[CH2:31][OH:35])=[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

8

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 7835EpichlorohydrinHCID 23703815Cetaben Sodium

Product 1

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

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 80711,2-DimethoxyethaneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 3.8 g. sodium 4-(n-hexadecylamino)benzoate, 3.7 g. of epichlorohydrin, and 0.7 ml. of water in hexamethylphosphoramide is heated to 90° C. for five hours. An additional 0.7 ml. of water is added, followed by 1 ml. of 1N sulfuric acid. The reaction mixture is cooled after 11/2 hours. After adding dimethoxyethane and benzene, the organic layer is separated and washed with water. The solvent is removed in vacuo to give a white solid which is recrystallized from 15 ml. of acetonitrile to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate. If this material contains any of the intermediate 2,3-epoxypropyl 4-(n-hexadecylamino)benzoate, it is removed by chromatography on silica gel.

Workup

  1. temperatureThe reaction mixture is cooled after 11/2 hours
  2. customthe organic layer is separated
  3. washwashed with water
  4. customThe solvent is removed in vacuo
  5. customto give a white solid which
  6. customis recrystallized from 15 ml

Sources & evidence

ORD record
ord-45689a00e7f844229273f399ada66367
Source dataset
uspto-grants-1979_03
Patent number
US04146546

Reaction notes

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