Chloroform → 4-Hydroxy-2-buten-1-yl 4-(n-hexadecylamino)benzoate

HRID 1439303Notes

Reaction equation

HRID 1439303 reaction equation
[OH:1][CH2:2][CH:3]=[CH:4][CH2:5][OH:6].Cl.[CH2:8]([NH:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(Cl)(Cl)Cl>CN(C)C1C=CN=CC=1.O>[CH2:8]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:1][CH2:2][CH:3]=[CH:4][CH2:5][OH:6])=[O:30])=[CH:32][CH:33]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 80652-Butene-1,4-diolHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 539426744-Hydroxy-2-buten-1-yl 4-(n-hexadecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a mixture of 8.8 g. of 1,4-dihydroxy-2-butene and 2.84 g. of 4-dimethylaminopyridine is added 4.16 g. of 4-(n-hexadecylamino)benzoyl chloride hydrochloride. The heat evolution is moderated with ice and stirring is continued for 4 hours. Chloroform and water are added and the chloroform extract chromatographed to remove any diacylated by-product. Evaporation to crystallization yields the 4-hydroxy-2-buten-1-yl 4-(n-hexadecylamino)benzoate as a white solid.

Workup

  1. additionTo a mixture of 8.8 g
  2. extractionthe chloroform extract
  3. customchromatographed
  4. customto remove any diacylated by-product
  5. customEvaporation
  6. customto crystallization

Sources & evidence

ORD record
ord-8f558aa388aa4f7597f042d1a962c691
Source dataset
uspto-grants-1977_11
Patent number
US04058550

Reaction notes

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