Benzyl Chloride → 4-Hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate

HRID 615064Notes

Reaction equation

HRID 615064 reaction equation
[OH:1][CH:2]([CH:4]([CH2:8][OH:9])[CH:5]([OH:7])[CH3:6])[CH3:3].[H-].[Na+].[H][H].C(Cl)C1C=CC=CC=1.Cl.[CH2:23]([NH:39][C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(COC)OC.CN(C)C1C=CN=CC=1.O.C(Cl)(Cl)Cl>[CH2:23]([NH:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]([O:1][CH:2]([CH:4]([CH2:8][OH:9])[CH:5]([OH:7])[CH3:6])[CH3:3])=[O:45])=[CH:47][CH:48]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

10

Reactant 5

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 612343-(Hydroxymethyl)pentane-2,4-diolHCID 132553224-Hexadecylaminobenzoyl chloride hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 213269404-Hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
10 °C

Procedure

A 13.4 g. of 2,4-dihydroxy-3-hydroxymethylpentane solution in dimethoxyethane is added to 2.4 g. of sodium hydride (washed free of mineral oil). After hydrogen evolution ceased, 12.65 g. of benzyl chloride is added and the mixture refluxed for 4 hours. After cooling to 10° C., 24.4 g. of 4-dimethylaminopyridine and 41.6 g. of 4-(n-hexadecylamino)benzoyl chloride hydrochloride are added. Chloroform and water are added after 16 hours and the chloroform extract is dried and evaporated to dryness. The residue is dissolved in acetic acid and hydrogenated at 30 psi hydrogen pressure over palladium black. After filtration and dilution with water, the 4-hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate is obtained as a white solid.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. extractionthe chloroform extract
  3. customis dried
  4. customevaporated to dryness
  5. dissolutionThe residue is dissolved in acetic acid and hydrogenated at 30 psi hydrogen pressure over palladium black
  6. filtrationAfter filtration and dilution with water

Sources & evidence

ORD record
ord-6d963bd4a3ce435a80c0f0f5b9540ab1
Source dataset
uspto-grants-1979_03
Patent number
US04146546

Reaction notes

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